My operating assumption is the Milwaukee real estate prices will double in the next 10 years, just like they did in the last 9.

If your rental is nicer, has off-street parking, and is updated the rents can be more than double $850.

The difference is that when I sold them after 2-3 years, they had doubled (or better) in value.

Or you could try to do a flip and double or triple your money in a few months then decide what to do from there.

Rumblings of property tax increases on STR’s in CA, CO and yes, even conservative Sevier County, TN.Sevier County's property tax on STRs basically doubled this year.

My wife has been begging me to look into STRs and I have stayed away mainly because I know and understand true long term rentals best.Our plan this year is to double our income and continue living on the previous budget so we can make a massive splash with acquisitions this year.

Our cleaner returned today to double check everything and found a tv remote missing (I know this happens a lot), chocolate stains in the carpet, more blood stains on other linens, bath rugs, and furniture, more furniture stains, etc.

I am 35 minutes away (roundtrip over an hour) on a Friday night and heading north from MA to NH would of easily double my time getting there. 

I suppose you could get a ratified contract and then do a double closing but the listing agent will probably want to see that you can pay for the property

A Double-Edged Sword?