As for why to sell, we own lots of vacation rentals in different areas (we just haven't sold any of them), and this is not one of the higher performing ones. 

I'm a betting man and I think you'll be looking for a refund of that $100.

I bet they made a killing there.Also I just thought of if you have family in other areas / states that you visit often you could look there or have them be on the look out for any good deals.

I wouldn't use him at all.Even if you're in a well populated area, your best bet is to go on a site like zillow and put in the address of the house you're looking to buy.Then filter for only rentals and see what they have in the immediate area.

For the lender to pick up more exposure, they tend to look at the performance in an asset and typically I have seen anywhere from 30-40% down and interest in the 6's.

@Mike MakkarI own several other rentals and so my personal residence could just be a very poor performing part of that business or I could just pay my mortgage payment to the rental business as rent.

The fax to PDF solution I mentioned might be good if the papers are distributed, but if they are all in one place and need to be scanned in bulk, then other high speed scanners might be a better bet.

If you're doing everything in Illinois, your easiest/safest bet is to form an Illinois LLC.However, an LLC may not be needed at this point.

You can buy performing notes which is passive and collect checks.

I would talk to the Board of the HOA and find out if they'll reduce or forgive the fines associated with these violations in exchange for a performance bond that you'll get it all fixed.Most HOAs just want the stuff fixed.