Generally that is something that will fall under their cost.

A little too hot for me at times, but I’m more of a fall guy

My biggest advise is to not fall for lower price tag deals. 

Any company insuring your properties without an inspection most likely has a clause buried deep in their policy allowing them to deny claims for conditions found on the property that do not meet their UW standards and they will deny you claim based on "the house should have not been insured with them anyway".Although the inspections can be annoying look at it from the other side.You pay them 1000 to 3000 a year to insure a rental property where they agree to pay out possibly hundreds of thousands of dollars if it burns down or up to 1 million if a tenant slips on a bananna peel and falls down the steps or the tenants dog bites someone and since you didn't enforce the tenant having their own renters policy to cover the dog bite the landlord's policy is paying out.The insurance company is very much like your rich uncle backing your business venture - you run the business, he takes on the financial risk from disasters, and doesn't even get a say in who lives in the property.Your rich uncle asking you to fix the steps, put up a handrail, etc which is in your and his best interest long term.Do you really want to rent out a property with a busted front step and a bad roof that is going to leak sooner than later?

The falling population is likely attributable in part to bleak economic conditions.

Contacted Aven as my deal was about to fall apart and got approved in about 1 day. 

While I wouldn't center a STR around 5 home games in the fall and a graduation, there is usually a lot more going on in these types of towns to keep it busy.

Glen Falls is a small market.

Unfortunately, there are also a few people who have popped up on BP trying to sell a crappy real estate-related program but fortunately the majority of the experienced investors on here don't fall under this category (plus the program spammers tend to get banned sooner or later).  

But if you buy four $200K houses then it's apples to apples and you're not going to fall behind.For what it's worth, I'd be concerned that if you over extend yourself buying a primary home you'll create a larger scale issue than just being house poor.