To get the best value on the work, is it better to contact tradesman directly for those repairs and then have the general contractor do the rest?

see if you think they have potential.if you can house hack, even better. 

Hopefully when interest rates go down and rents go up in the next 2-10 years, we can refinance and have better cash-flow.Option 2: Pay with cash right now (~1.3M) and with a ~7% cash-on-cash return we conservatively net ~7-8K/month and properties appreciate with inflation.

I thought I get on the forum and see if anyone here has COSTAR and wants to split the cost and I can pay them monthly or if there is a better way to utilize costar and not pay 1,000 dollars a month.I thought I asked before I signed up with them, if I have to eat the cost I will but I need to know if anybody here knows anything 

If you're making decisions based off of fear of what others think of you... then you might be better off buying a nice multifamily property and living in one of the units. 

I believe this is a much better and faster return on my investment and is a smarter move all the way around because I won’t have to get town approval to rent garage space like I would to turn my duplex into a triplex.

Do you have any recommendations on which cities/ zip codes you find better and which company would you recommend for property management?

Better to buy fewer but higher quality properties.

With both of these strategies, I would look at the rehab as a way to bring up market rents so you can cash flow a bit better, and just sit on the property for a while until you can build up enough equity to cash out or sell. 

This is putting downward pricing pressure on the classes below it, as people move up for a comparably better unit at a relatively reasonable increase in cost.