That can literally be like 50 bucks - and that is not up to youInvesting in section 8 usually means C-D class areas - Higher risk, higher turnover, higher chance of evictions, higher chance of property damage, behind on rent etc.Instead of buying a 20 unit, maybe considering scaling down and investing in a solid area. 

Will this affect my chances of finding lenders?

You can minimize your chances, but the chance is never zero.

I say never thats not accurate but 99% chance no one will.. so just sayin.. depends on  what your plans for the property are.. of course if your flipping it and a buyer needs title insurance you are stuck

We often get a reply like "Everything's great but the coffee maker isn't working" which gives us a chance to have a new one dropped off and get ahead of any issues.We also provide toiletries and basic cooking needs to all guests.

The primary reason is because the property is vacant and a number of independent contractors are in and out of the property thus increasing the chance of a claim or loss.

It might help you out if you're a hammer swinger type guy who can produce workmen like quality results versus homeowner DIY results.Someone who has been in this business for awhile , and brings a lot more knowledge , and contacts to the deal we'll have a lot better chance at performing a turn around on the property then to someone who is new and inexperienced. 

Will this affect my chances of finding lenders?

Affordability or lack there of has the best chance of slowing this market but there appear to be plenty of buyers in all price ranges.

If this was your first year getting a 1099, then there might be a small chance that you could get away with just this year's 1099.....HOWEVER, since you have been 1099'd for 2 years now, then the mortgage lender may request tax returns before extending a mortgage.