So I stepped it back, thought outside the box and removed the specifics of real estate and wouldn't ya know I found long standing models that were widely used for the exact same situations.

HELOCs on investments could be applicable but these programs are not widely available qualification is usually not asset based

They’ll help you map out what’s deductible under each scenario.Run both models side by side (with & without personal use).Use tools like AirDNA or Mashvisor to estimate cash flow.Check local STR rules in Fairplay—some towns in Colorado are getting stricter on licensing.You can definitely blend lifestyle and investment—it just helps to go in with eyes wide open so you’re not surprised come tax time or when evaluating long-term ROI.Let me know if you want a simple tax comparison spreadsheet—I’ve helped a few folks model out these exact two options.Thanks, Kyle Wheeler

Our association is county wide and just starting back up after having been long dormant.

Enforcement on a wide spread scale will NEVER happen.

I've seen a wide variety of these from $100 annually to almost $600 per month.

I would recommend connecting with an experience investment specific broker who can help you compare programs across a wide variety of wonders.

I believe just as with almost everything under the sun, a wide range of people exist in the syndication space.

From what I've gathered, Santa Rosa is not STR friendly, nor is Sonoma County in general because of a strict county wide ordinance.

Be kind to yourself and feel free to send me a DM if you think that I can be helpful resource.That makes sense but yes I do have FOMO, house prices have historically increased faster than rents, thats a nation wide trend.