You are literally losing out on thousands of dollars of income annually by gambling on appreciation.

@Brianne H.It is always a bit of a gamble working with someone new. 

You are no longer investing you are gambling that the rents appreciate or you can refinance the property into a positive CF position before you run out of money. 

But also return on investment is better.A gamble for a newbie, but can be a way to learn the business.And go for the smaller properties.

Unless you just really like gambling or have money to burn, in which case, by all means - roll the dice if that's your thing.Further - contractors and suppliers are SO damn busy these days with all of the construction going on around here that getting a renovation of any real scale completed correctly or a new construction job done is a very serious challenge in and of itself and takes a great degree of skill, care, TIME, connections, and probably some luck.

Would you really want to gamble on continued appreciation, instead of cashing out?

Probably a slight loss after the second set of closing costs, and that's with the gamble that interest rates don't rise.Option 35.5% for commercial loan 65% LTV for cash out. $357.5k5 year balloon, 25 year amortization10% line of credit at prime +1One plus here, I won’t be paying interest on money I’m not using.A big concern is timing.

One issue i see with doing it the way you're thinking is that in our market in Miami the gamble is much more risky, with the crazy high rents in those areas you mentioned so you have to make sure that area can be constantly rented out, otherwise you're gonna have to bite that monthly lease payment.

Until you have the keys and your name as owner, it is all a gamble on whether anyone will want to bid on a project that might fall through.

I am a search and rescue/EMS helicopter pilot for the offshore oil industry in the Gulf of Mexico.