Or worse case in the S&P 500 (all a gamble I know)3) If I keep it, buy another home then I guess I can sell it in 2-3 years and not pay capital gains on the appreciation but if I make say $175 a month cash flow (after PIPI, 6% maintenance, 9% vacancy, no management as I would manage it while I was local) in 3 years the roof (partially) will for sure have to be considered a sellers concessions which would remove a chunk of that equity/cash flow I just built up but if the home goes up in value that could negate that.Current monthly is $1650 (that includes HOA) - Would rent for 2500Taxes are low (based off 215k purchase price) but im guessing if I convert it to an investment property and remove the homestead it will jump up to the new appraised level?

I'm taking the gamble that I can finish the 6th unit and get the zoning modified somehow to further increase casflow.

They just change the subject and the latest story is that, "We took a gamble and it didn't work".

Versus doing one large building, don't want to take the gamble, thus we will stage smaller buildings as they fill up.All units will at least have one 12 wide x 14 tall (clear height) panel door; 16 foot eaves. 

Not because both are gambling, but because both have the same definition of what a loss is, and both have the same rule for avoiding that loss.Question:  If you sat down at a Poker table with a stack of chips, and after the first 5 hands that stack was cut in half, how much money have you lost?

C) If I want to gamble on consumer sentiment, which is what I consider all publicly traded equities, than I will at least gamble in an area with better appreciation potential.C is the biggest reason.  

I wouldn't expect it to be lifted until 2022 but hopefully I'm wrong.Anyone investing in rentals in C- properties in NY EVER is taking a huge gamble.

and refunds to guests2) Hire amazing people - cleaners, handyman, recruit some neighbors to help fill in the gaps, & self-manage or hire an offshore VA to manage the property if you'd rather make yourself rich instead of making a local property manager rich (more on that here: https://www.biggerpockets.com/... )And make sure that your cleaners and handyman are not only doing a top-notch job of keeping the house in pristine condition, but they are also reporting to you (or to your PM or to your offshore asst) every little thing that needs to be upgraded or replaced so that you can stay on top of it and take care of things before you hear it from your guests in the form of guest complaints and bad reviews.

The more you filter your list the smaller your list and the less chance you have to make a deal.Lists are just an other word for "gambling".

Invest don’t gamble.