BUT I feel like I still have to have a ton of involvement especially with multiple rehabs etc, to dictate what expense is from what property and what the purchase was for etc. to be sure deductions and depreciation are correct.

It's not worth the extra monthly income that comes with getting involved with low income renters.

I’d love to have real estate provide some financial freedom/flexibility and create a portfolio that I could eventually get my kids involved with and pass down to them, but I end up feeling frozen/stuck based on the factors above. 

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). 

I want to slow my life down a bit and enjoy the fruits of my labors (I had cancer a few years ago and I acknowledge my time to enjoy life is finite).It occurred to me that I should just cash-out refinance my properties that are fully stabilized and that have significant equity, but that can also easily support the new debt incurred. 

This stabilization period is expected to be short-lived, creating a window for strategic investments.

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. 

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.