If you kept a similar property and skipped §121, did the future appreciation justify the tax trade-off?

Right now wholesalers are mainly doing:SMS TextingCold CallingDirect Mail / PostcardsThe “next level” is PPL (Pay-Per-Lead) through lead generation companies, so you’re only paying for conversations that raise their hand.Most people start by pulling lists of sellers in distress (pre-foreclosure, tax liens, probate, divorce, etc.) and then stacking those lists so you’re not just hitting one pain point but several.On top of that, a few other things are working well right now:PPC / Google Ads – motivated sellers often search “sell my house fast” before answering cold outreach.Facebook/Instagram Ads with strong local targeting.Driving for Dollars apps (batchdriven, dealmachine) paired with skip-tracing to hit niche properties others might miss.Follow-up systems – 70% of deals come from nurturing leads over time, not just first contact.What seems less effective today:Bandit signs (cities are cracking down, saturation is high).Generic postcard campaigns without a targeted or consistent follow-up strategy.Mass cold email (deliverability has dropped a lot).The real key is consistency + multi-channel.

Your logic says I should save driving time by skipping my seatbelt.

A lot of investors just skip HOA properties altogether because of this kind of restriction.

For example, this would consist of; pull a small list in PropStream or Propwire, skip trace, then text with Launch Control or call with BatchDialer.

Thanks, yes, renting out a room as a STR is legal in NYC but that's more-or-less limited to people who are essentially running a bed&breakfast type situation (no thanks!).

I would use sms with launch control and use deal machine as a list provider and skip tracer.

Build buyers first by calling active flippers and PMs to get their exact buy box; use free/low‑cost tools like Google Voice, Google Sheets or Notion for CRM, Zillow public records plus trial data tools for skip tracing, and DocuSign with an attorney‑reviewed assignment.

Also, great point on property break down, the one benefit I do have getting back into it is that I was a GC for almost 10 years and can do repairs at probably 30% of what an investor hiring one can (I know sub crews and how to order materials at cost so I can skip most markups) but, right now, I just need more stable income before I get back into it. 

Keep refining your “driving for dollars” list, and maybe layer in skip tracing to reach owners directly.