I've been using "Subject To" and other various creative techniques for thirty years and I've learned a few things along the way that may make it easier and less risky if you are trying to use them yourself.
1) First,...

The questions rellay is how much of these trades can he replace. 20% or 80%?

The trade-off is you’d carry the refi risk in 2031 (interest rates could be much higher, and you’d pay closing costs again).So it comes down to your goals.

Depends on your market, but in general I would not trade market rent for vacancy unless I was in danger of losing the property or otherwise in financial distress and no vacancy was a necessity.

I have worked with a number of investors looking to trade up with a 1031 into a new build multifamily. 

Get a RE license, become a hard money officer, learn the GC trade, wholesale trade. 

The trade-off is that appreciation is more linear; it's not the same rocket ship upside Woodlawn has, but the cash flow stability tends to be better.How I’d personally evaluate it:If I want cash flow + stability, I’d lean Pilsen.If I want long-term appreciation + can stomach tax volatility, Woodlawn.Run both pro formas with the future tax number, not what's listed.

Lead with a simple credibility stack: be clear about your buy box and pricing logic, share a one‑page deal sheet on every trade (collateral, payor history, servicer notes, exit plan), and match your promises to your updates.

It aims to redistribute US trade revenues to American citizens, excluding high-income earners, and is framed as a "reward for hardworking Americans" who support domestic production.

It was a true trade-off as the Logan area is more limited in STRs and new builds so ADRs are higher and likely to stay there compared to RRG where the market is headed towards being flooded and there's the potential of ADRs going down like in Gatlinburg/Pigeon Forge area.