@Shelly Shanks For buy and hold the formula is relatively simpleAnnually:(Monthly rent x 12)- property taxes - insurance -property management fees - HOA fees if applicable - budgeted maintenance and repairs- expected vacancy - loan payments.This will give you your annual cash flow. 

I keep a detailed spreadsheet of each repair item and the name of the contractor or sub responsible for the repairs. then I use the spreadsheet as a checklist.

Also, I added a "maintenance/repair" category for minor things like fixing a leaking toilet, broken window, etc.

Roofs on all the buildings needed to be repaired, with the largest office building being the first.

I made the repairs, and still told her she had to leave.

Secondly, many condo associations are run poorly and have little in the way of financial reserves, so unexpected repairs, maintenance, or upgrades could translate into surprise special assessments that will gobble up your profits.Flipping off-market properties is a sound strategy, but it requires serious marketing effort.

I have put $40k in renovations to both of them (they flooded and needed extensive repairs).

Since inside condition is unknown you need to make assumptions of repair cost.

I understand that I can get a much larger house with only needing 3.5% down, however the repairs and upkeep are still going to be scaled to the larger size of the house.

Now you have to do your repairs which will probably cost you way more than the damage deposit, and time before you get a new tenant in...