Having the seller carry a second is not a problem for the first, as long as their business with you is finished and the loan has closed.

Three and four units properties tend to be slightly more investor facing, but there are still a lot of regular buyers that pick up three and four units as well.

I currently own and self-manage two STRs in Maine and should be closing on a small 'cabin campground' with 10 cabins nearby that will also be operated as STRs. 

@Elmer Urias I ended up buying a vacation rental on Emerald Isle NC instead of Ocala.

Since you're so close to Loyola and not too far from Northwestern, I imagine you might have a pool of people who need temporary furnished housing while they study, do a medical rotation, or travel in the medical industry.

Often, owners beat up PMCs for a low price, but fail to understand the PMC will often cut corners to make sure they are still profitable. 

I will say we are way out of town with just a small market close so it makes sense to have a fully loaded house.We only provide 2 small soaps and 2 shampoo bottles in each bathroom.

As I read your post, the reoccurring theme that came up was a screening problem. 

Here are a few examples: https://fourpeaks.box.com/s/heitpydgv3s6gtbiudszgtglhzn7gj29Our park size is usually 40 spaces up to about 230 spaces.

If you end up in Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods to give yourself an in depth idea of the market.