Lastly, surround yourself with experienced investors who can offer advice and support along the way.

At this time we're not considering it so I'd like to just keep it to FL and surrounding areas. 

In fact, you can't get a new vacation rental license in either city, nor in the unincorporated Summit County that surrounds those towns. 

Do a quick market analysis… go to rentometer.com and see what it thinks your rents should be based on the rentals surrounding your properties!!  

Also, concerns surrounding potential valuation corrections in this market had me thinking it was probably best to pull my capital and redeploy into a more 'stable' market/LTR. 

I'm interested in two of the properties on the Montgomery County PA Upset Sale list as they are in my surrounding neighborhood and am actually a casual acquaintance of the Owner (which may not be a good situation, particularly if I were the successful bidder).  

I live in River North and preferably would like to work in downtown Chicago and surrounding neighborhoods but open to the suburbs as well.

An old tv infomercial championed you to get rich quick and sit on the fan tail of a Luxury yacht sipping a tall cool drink surrounded by swimsuit clad models.

So my 5 bedroom new construction on top of the mountain with phenomenal views is lumped in with a 30 yr old 5 bedroom 1/4 mile away in the valley surrounded by trees.  

I would like to get your thoughts on the area you are in and other surrounding areas.