At a certain point, the return drops low enough that they should sell the property and reinvest in a new property (or properties) that will increase the return dramatically.

Since short-term rentals in the US could become over regulated or downright illegal (where they aren't already), the resulting cash flow and profitability could drop hugely if not becoming downright negative in case of a conversation to long-term rental.

He'll probably drop price for that alone, but not, who cares?

I've made the mistake of giving out special treatment before and it's unrewarding. rent is due on the first, eviction starts on the 5th. carve that in stone and drop it on the front lawn. it's NEVER changing.

What you need to do is once you get that, find out how much it will cost to fix the items and then negotiate with the seller to lower your price.If house prices drop in the short term, it only matters if you plan on selling or refinancing. 

I had to drop everything and head over there, try to figure out why there was a huge puddle of blood on the floor and at the same time improvise a quick temporary fix for an (unrelated) leaky pipe.

First thing I would do is determine if there's need for it in the marketplace and get a temperature check on the political climate in your area.

Aside from that, having partners may allow you to progress faster than you would on your own as you are not likely full time in the biz yet might not be available all the time to drop your life and take care of something investing related but with partners you can address those issues more easily.Many people have had great partnerships.

I really don't want them to pay the claim and then have my rates go up or possibly drop my policy (not likely but worst case scenario I guess).

I doubt that many students or younger people like the idea of sending their rent checks through the mail or even dropping it off.