Eventually when the property sells, you will have long-term UBIT, which is about 20%, and remember the carry forward loss capability.

Outside of wholesaling, I'd like to explore BRRR, Fix-n-Flips, and eventually Multifamily properties. 

A matter of fact, I had one a decade ago, a full IRS field audit, and passed owing $0.Eventually I want to have a couple hundred properties, and more installment sales.

So, I would move to a 2nd gas heating system eventually.

If you hold it long enough it will turn green eventually.

So really, flipping isn’t about tax advantages—it’s more about building up some solid cash reserves so you can eventually invest in buy-and-hold properties, where the real tax benefits start to kick in.

Idea is I could “trade-up” houses, get some trapped equity out of condo, and eventually keep this in my portfolio long-term, for a similar PITI.

Here are the Positives:Upfront Payment: The tenant’s offer to pay the full year of rent upfront, along with the deposit, shows a commitment and provides financial security for you in the immediate future.At least She was Honest in Her Communication: The tenant has been transparent about her situation, which can be a positive sign of reliability and sincerity.My Negative Concerns:Her Future Financial Stability: It's only a one-year lease, if her medical condition and financial condition should worsen (Heaven forbid), you may have to face her wanting out of the lease earlier than the 12 months and eventually you may be faced with having to decide not to renew the lease (after her 1 year contract is expired) based upon the sad news of her condition becoming worse, (Heaven forbid).  

Eventually, I realized I needed to back off.

If you use insurance to make ordinary repairs, it will eventually drive up costs.