Looking to Invest in either STR, Single-family, or Multi-family

[Virgil Gonzalez]

Hi Bigger pockets,

I am a new investor in my early 20s with a stable income, good credit, and +30k in savings. I am looking for the best way to start my portfolio with either single-family or multi-family homes in Long Island or Westchester with the intention to buy and hold. Currently, I am negotiating to go under contract for a fully renovated duplex in Yonker, NY that I intend to owner-occupy under SONYMA DPAL. 
However, with this method, I will not cash-flow while house hacking unless I refinanced and removed the sonyma restrictions in the future, or obtain secondary investment properties via built-up equity.

Due to the competitive market in New York for a multi-family with preapproval only for 600k, it seems my only other options are to explore Single families in-state or Short term rentals out of state. Does anyone recommend short-term renting i.e Airbnb either buying or renting out a condo? I am open to Florida, Texas, New Jersey. I understand Florida has condos identified as short-term friendly with no restrictions to leases. What are some of your experiences as first-time investors looking to build your portfolio either by arbitrage or buying, holding rental properties?

Would appreciate all advice before going under contract, thank you!

[Obed Calixte]

In regards to Florida condos: you may find it harder than you expect to find STR friendly properties that can be financed with traditional financing (ie, conventional loans) -- if traditional financing is your plan.

Condotels (condo + hotel) inherently are STRs but are considered non-warrantable by Freddie and Fannie, and therefore do not qualify for traditional financing. You would have to go non-QM, hard-money or private financing route.