Due to personal faith based reason, I prefer to only invest in all cash deals that don't involve traditional financing (so typical passive RE options like syndications, RE funds with fixed returns, REITs etc are not a viable option for me). 

STR has a lot more risk given the seasonality swings and I cannot understate the time involved in bookings and customer service.Having said that we DO have STRs here in St Augustine, Florida in prime areas in the $400s. 

I bet you don't have any friends who want to do this at your age so when you tell people about your dreams they say it's crazy.

The biggest challenge was resolving the parcel recombination, which involved acquiring additional land and coordinating with the city for approval.

The biggest challenge was resolving the parcel recombination, which involved acquiring additional land and coordinating with the city for approval.

While its nice to borrow as much as possible, the risk involved can sink someone as in most instances their is personal guarantees involved and lenders will bankrupt sometime to try and get every penny they are owed. 

As a new investor, your best bet is to start small with an app like DealMachine or Propstream so you have direct control of your options.

These platforms do not get involved in the transaction beyond the connection, and so any liquidity options and investor may have are simply what that sponsor has or has not offered in that individual fund/deal.

I'm opening my second home and find them extremely rewarding but think I may stop at these two because I am extremely involved in them and am spreading myself too thin I think. 

The potential for a loan call is higher and higher with sub to the more parties you involve if that makes sense.Trying to take down four homes sub to and then do remodels to them all, and then list them on short-term rental sites, and get full permitting and ok for not just the STR, but for your renovations and all prior renovations maybe done without a permit, while on subto, sounds like a pretty big mess to me.I would consult with a sub to specialist and prepare for the potential of having all the loans called at some point.