Eyestabber,
First, stop playing 1.13. It's a terrible user experience today. NCTH and NIS add tactically and strategically meaningless complexity (the think to click ratio plummets in 1.13), and everything is half implemented or buggy. There's also some really cringeworthy stuff like the "racism and sexism" system.
I recommend using Stracciatella.
Here's how I recommend you approach the beginning of the game:
To begin with, hire a merc with a long range weapon, good physical stats and marksmanship (Shadow, Magic) and a merc with decent leadership and physical stats (Scully, Stephen, Len) on one day contracts with equipment. Also hire Dr. Q with no equipment, also on a one day contract.
Do *not* make an IMP (yet), do *not* hire bottom tier mercs (unless you enjoy grinding).
Obviously, the first order of business to clear out Omerta, talk to Fatima, and hire Ira. Give Dr. Q Ira's armor, medkit and a canteen or energy booster (if available).
Now, take Dr. Q to San Mona and do the leather store quest for $10,000. Use this easily earned cash, in combination with Dr. Q's martial arts skill, to make another $15,000 at Darren Van Hausen's fight club. This also earns you an audience with Kingpin, who you should pay a visit (he gives you a quest, and more importantly, summons $20,000 on his person). As the leather store owner told you after you rescued his sister, there's $30,000 begging to be stolen in the abandoned mine, so do that. You could stop here, but there's more fun to be had. Get Dr. Q to beat up Billy at the Shady Lady, and take his Mini-14; kill the proprietor of that den of iniquity for another $1,000 or so and camp in that corner sniping or beating up any adversaries. With care in your tactics, the sector should be clear of henchmen quickly and you should have some nice lower mid-tier loot. Next on the agenda is Mr. Van Hausen; the idea here is to close the door to the club, and surprise karate attack him. As soon as he's unconscious take cover underneath the bar table and finish him off with your Mini-14. AFAICT, this is very heavy cover, and it's highly unlikely the enemy can hit you firing from the entrance door (but you should be able to hit them). After a long, boring and drawn out firefight you should be victorious and another $25,000 richer. Now proceed with care to take out the rest of the sector, noting that enemies camped in buildings face a certain way and you can surprise them from behind shooting through the windows. Hollow point ammo shots to the head work well on Kingpin's men. Killing Kingpin himself will earn you a nice Steyr Aug and your final $20,000.
IMO the entirety of San Mona should not have been included in the game, because it's just a free $100,000. There is no real strategic trade off (just the $1,500 opportunity cost of hiring Dr. Q).
In the meantime, your other squad should have taken Drassen. Leave Ira behind to train militia at Drassen mine, and continue to Skyrider (a woman in C13 will give you a hint as to where he is) and the SAM site (D15).
You will want to make some strategic choices at this point. Extend the contract of anyone you like to a week and hire some fresh talent. Good additions to your main squad are Ivan, Raven and Lynx. Cheap teachers (Fox, Hitman, Wolf, Stephen (the latter two are good enough to be main squad guys)) are also a priority . You will be taking at least two strategically important locations (mines, SAMs) a day, so you need to get good instructors in there to defend them. To this end, make an IMP with 85 leadership and expert teaching (IMPs are not suited for combat roles unless you want to grind).
To finish off Day 1. Dr. Q should be able to take the D2 SAM site and Chitzena with ease (thanks to his newly acquired Steyr AUG).
AFAICT, any other way to start the game is a self imposed handicap (at best) and "roleplaying" (at worst).
On day 2 you should concentrate on taking Alma and Cambria, priming yourself for an assault on Grumm on day 3.