The house has appraised for $335k, my hard money note is for $242k, and I'm looking at only about $15k out once closing costs, taxes, and insurance are accounted for.

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Not going to give here a lecture on S-corps, but take my word: no benefits, only extra hassle and extra cost, such as preparing another tax return.

Very few non-owner occupied property policies guarantee full replacement cost - they typically provide replacement cost up to the dwelling limit purchased. 

It appraised for $201,000 the other month and I put $103,000 in my pocket after closing costs and paying off the old note.I wish I had about 20 more of those...

If you live in a high cost of living area, investing in more affordable out-of-state markets can be a great strategy.

Once you pay realtor fees, closing costs, sellers want 10k for points and concessions.

I will not expand my business to areas without having a good team first. 20 to 25% is reasonable if you come across a good PM near you, there is a lot of work that goes into STRs 

It is also for that very reason that you should be wary about going in as I do feel that the Pittsburgh has gone pretty high up in it's property values. 

It also saves you some costs, which is helpful when you’re just starting.