Hi Joseph,Timing the market is very difficult to do and you are better off making decisions off current numbers rather than expected ones.

Hopefully you find one sooner but it will frame your expectations the right way to avoid getting discouraged in month 6 especially in a hot investment market like today.Real estate is a long-term wealth game and it pays to be patient.

I don't know your market to know potential purchase prices, rental rates, your DTI for loan qualification purposes, what would qualify as an upgrade in your market for VA loan purposes, vacancy rates and expected maintenance costs in your market, etc. 

How does your PM handle a tenant who breaks a lease early and in accordance of the lease, now loses the deposit he/she made who leaves the house dirty, broken blinds, cracked window, etc So there are issues that normally would come out of the deposit to fix?

That being said, it could make more sense to you to buy for low to moderate cash flow but strong appreciation, versus the other way around.If you want buy and hold rentals, I’m hoping your idea isn’t to tie up all your cash in ONE property, but rather to get your own traditional investment loan or creative financing from sellers.Another consideration is many speculate we could be nearing the top of a real estate market cycle, with a dip in home values expected when you could pick up some better deals.

I had been anticipating a hit but did not expect anything that drastic. 

It's a numbers game, though, so expect a 1% call rate, which is around the industry standard.

You can not now expect any money back. 

In the same 3 to 5 years, you can exceed your expected ROI with much less risk and very little work.

@Kyrstin Szewczyk first of all this is the best way to ruin a friendship so tread lightly and get everything in writing and make sure you all understand your duties and you are all on the SAME page and have the SAME expectations.