Freddie has similar intricacies, but also does not require a two year history of receipt; https://guide.freddiemac.com/app/guide/section/5306.4If you can use the rental income to drive the DTI down so that you can reduce the down payment similar to that of the FHA product, the benefits of the conventional option will outweigh the FHA option, as I'm assuming you have a strong FICO based on rate quoted with no points.  

I recommend that you speak with a real estate accountant to see if you will benefit from a cost segregation first. 

Especially related to Vacasa, Evolve, some of the other big name managers.

For a relatively "safe" creative financing, one needs serious reserves (lots of moolah) and the ability to sell or refinance quickly when one of those "hiccups" occur.The gurus usually collect a large fee, from people who have neither money, reserves, nor experience.

With that being said, and to be transparent, I have had a harder time finding investing partners on the last property I bought in La Fortuna which I think is related to the change in the economy.  

What are the potential pitfalls and benefits of each approach?

If you are living there, then you need to weigh the benefits of having a home, as oppose to renting somewhere else.

Related damages:When tenant took possession, the living room had a vertical blind set apx 70” long (covering two windows.)

If you work with real estate investors, it's nice to be relatable to your clients as well. 

My HOA pays for everything related to the structure and my cash flow is $200 after HOA dues so I only tend to keep 2 months of rent in reserves per unit + the tenant deposit