Financing and Scale Up

[Eric Dyson]

New to real estate investing and trying to learn as much as I can before taking the plunge to purchase our first property.  My wife and I are also trying to figure out if I qualify for PSLF loan forgiveness for school loans.  Once we figure out our plan there we will be ready to dive in. 

We are interested in long term appreciation, mortgage pay down, tax benefits at this point rather than cash flow as it relates to short term rentals. My W-2 income is more than enough and we will continue working until our investments are producing enough income. The sooner we get to that point the better.

I'm thinking ahead to the 2nd/3rd+ property. I want to structure my plan so we can scale up quickly. Ideally I want 4-5 STR that pay for themselves in terms of mortgage but with appreciation/tax benefit/mortgage over 5-10 years are able to provide a sizable income.

The easiest way to start seems to be second home mortgage for 10-20% down. Then any additional properties would require 25-30% down as an investment or DSCR. I can do that but to save enough for each additional property would take 2-3 years per property. (Thinking properties valued at 1-2 Million, in high occupancy regions). I can accomplish the 4-5 properties but it would take 10 years to reach that point to round out my portfolio. Is there a way to structure financing from the get go so things can spitball quickly and we can get those 4-5 under contract in the first few years?

As an aside I am a surgeon with a high W-2 income but less available time due to a demanding job.  We like the idea of Maui and Sedona so these would be long distance ownership situations. 

Any advice would be appreciated. Thanks in advance!