While vacation rentals aren't a huge drop in the home supply bucket, they're not nothing, and any reduction in home supply for primary residences will eventually push prices up.

I just got a renewal and the policy went up 67%, makes it hard to consider continued ownership of the property.

Do you find that your listing inquiries pick up closer to the availability date?

Although you can call the existing reservations and give them a heads up and link to the new listing.

Even if I start with one property and work my way up from there, I’m certain I can be good at it.

@Faaz HafidI am actually expanding to the MA market and under contract on a duplex in that same street.Did you end up buying this property?  

Now it seems to start at $150 and go up from there. 

I would encourage you to do the following to set yourself up for success -1.

Family status is the protected status that trips up most people, with comments like great family home, great neighborhood with lots of kids, this is the ideal place to raise children, etc. are clear violations of fair housing rules.

As a direct short-term rehab style ender we lend to NEWBIES 100% of purchase & 100% of the rehab on 1-4 unit properties (in 18 states) up to 70% of the ARV.