When the VC moneydried up, they had to drastically raise their flat fees, but were still out of business within a year. 

The previous owner took exceedingly good care of the building and there was nothing that need to be done except to raise the rents.

If you are doing long term rentals and raising rents, you will have turnover of a significant number of tenants after their year of renting when you raise their rent.

I always bill back water/sewer/trash before raising rents. 

if there is appreciation, but you wouldn’t sell your current home tax free and buy a neighboring home to rent out, (There by raising your cost basis for additional depreciation and lower capital gains tax.) then it probably doesn’t make a good rental property. . 

Certainly nothing ground-breaking in terms of ideas here, however I'll be very hands on (and on site) during the process to make sure that every step of the way is executed to a high standard and very carefully.Once I've hopefully developed a successful track record and gained experience, my next goal would be to move on to commercial assets (think multi-family, industrial etc) so that I can leverage my existing investor network and real estate knowledge to raise 3rd party equity and take on bigger projects.

Unless you were raised in or are from one, you have no idea.

I wish you would have told us the year, it makes a huge difference.Anyway, everything you mention, plus 1) get a camera run on the sewer line, 2) make sure the Elec panel is newer and sized correctly (a lot of HIs will just say if it's functional or not) 3) Foundation ( is it slab or raised?)

Some lenders would raise the 20% with private investors through PPMs or unsecrued notes bank does not allow junior loans.

There are also ways to go about mindset shifts if that's a serious issue, but I don't know, it sounds like you've spent time with this property, you know all about it, and you have a bunch of other stuff going on in life.For instance, you decide not to raise rent all the way to market rate....This is probably a good move if you hate maintenance calls and your tenants know to handle some maintenance themselves because they are getting a bargain deal.