At the beginning, it may be difficult to get a more expensive property that will appreciate well and so your choice is go with the cheaper property and get cash flow until you can sell and upgrade, or wait for a really good deal which you may be waiting for quite a while and its possible that you will have spent so much time waiting that you could have purchased multiple cash flowing properties by the time you get a good appreciation deal that you can qualify for / refinance after the rehab. i know anyone can go out and get seller financing deals, HML, flip to build capital or whatever the case may be I am just saying sometimes those will be harder and could result in less deals overall. 

There are several articles that do an exceptional job of explaining who, what, where, why and how tax payers qualify for the ‘STR Loophole’ listed here:The Short Term Rental Tax Loop Hole: A Game Changer for W-2 Wage EarnersThe Short Term Tax Rental Loop Hole: What Investors need to know The implications on the Oregon and California Coastal STR market is a strengthening buyer pool for luxury rentals in the $750-1.5M+ range.

But, you may want to check out Bryt Software, it was a real game changer for us.   

.#1 NUMBERS GAME:  It's not easy.   

Hey @Brendan Lim, what is your projected 5-year IRR (or Equity Multiple) on this investment? 

At one point years ago, I toyed with the idea of owning giant apartment complexes in multiple cities.

You will need to be ultra conservative on your numbers and have multiple exits.

The calculator is a LIVE excel with multiple tabs and all of them are interconnected, you may mess up a formula and you will see awesome returns inaccurately.

I understand it isn't easy, especially when new in the investing game.  

You can target lists through a multiple list source sites, skip trace those lists, then market to those buyers through cold calling, SMS campaigns, direct mailers, and/or door knocking; amongst other routes.