And then hold.To me, I'd suggest you look at smaller towns that have good schools and are close to cities so that you can get houses closer to that 200k or less mark yet still have a shot at decent appreciation and decent rental increases over time.

I have a local agent in town that I have kept in touch with since we moved here. 

Our major focus has been developing two larger (for us 220/365 units) locations in a larger town and we haven't looked back at our original locations. 

That's what happened to many of the towns in 2018 - entire towns under water - but no one had flood insurance.

. ** I’d ask for their Airbnb or VRBO profile link to review their reviews, years hosting, etc. to ensure it lines up with what they’re telling you*2.) with you guys being out of town, I’d make positive they have a team of maintenance guys for whenever something along the lines pop up.

I called 4 other companies in town and they all quoted 8-11k.

Don't worry about that as there are different ways to get to town and different companies might use different terminology.Work with a knowledgeable agent that talks your through your risks and don't try to conceal what you're actually doing. 

We made an exception, because he said that he was coming into town for a funeral. 

As rents and home prices rise, long-time residents are being squeezed out.Worcester is increasingly becoming a bedroom community for towns like Marlborough, Hudson, Natick, and Framingham, as those areas become more expensive.

However, a major employer pulling out of the town your rental property is in could severely impact the rental market, cutting your rental income.