I don't believe having an S Corp stops you from becoming a "Dealer" or not, but flipping is earned income and taxed as such whether you flip in your own name, an LLC or an S Corp LLC               "Doing your flipping and wholesaling activities through a corporation (which is a separate taxable entity from you personally) will prevent you from personally being tagged as a dealer thereby preserving these tax tools for you."

The long-term side will remain passive, but if you materially participate in the STR (100+ hours and more than anyone else) and meet the average stay test, those losses can be considered non-passive and used to offset W-2 or other active income.The long-term unit = passive activity, losses suspended unless you qualify for REPSThe short-term unit = can qualify for the STR loophole if average stay ≤ 7 days (or ≤ 30 with services) and you materially participateKeep the STR activity reported separately to preserve the loopholeSTR losses can offset active income, while long-term rental losses remain passive

It keeps tenants happy, minimizes emergencies, and helps owners preserve their investment.

Others want tighter control and are willing to risk turnover to preserve condition.

So that withdrawal rate implies being able to spend 5% of the initial portfolios value and continue withdrawing to support the same real spending in perpetuity.The bugaboo of retirement spending is inflation, to the point where the high inflation years of the 70s and 80s made it harder for retirees to preserve their purchasing power than for those retirees who retired right before the Great Recession!

If you have something in Ohio that you're working on/I'd be happy to look into it for you@Craig Cann preserve hardwoods when you can or use LVP when the floors are relatively level/not slopping.

Your primary trade-off is now clear:Access Equity Now: Accept the $1,400/yr tax increase and the other tax consequences (like your dad's depreciation recapture bill) to get the DSCR loan now.Maximize Future Wealth: Leave the property in your dad's name, avoid the tax hike, and preserve the massive benefit of a stepped-up basis upon inheritance.The other tax questions (gift tax, depreciation, etc.) are important, but they are secondary to this fundamental Prop 19 reality.My immediate advice is to model whether the deal still makes financial sense with the higher property tax expense.

If it’s cash flowing well with appreciation upside, a HELOC/HELoan keeps your equity working while preserving the asset , especially smart in today’s market if rates on new debt are higher than your current mortgage.With ~$100k, you could structure deals for 1–2 properties depending on the market.

Open space and preservation tends to be a more vulnerable target.Regulation is one of those amorphous bogeymen (or women!).

A well-designed asset protection strategy limits liability, preserves wealth, and strengthens your defenses if challenges arise.To navigate these areas with confidence, build a team that includes a tax professional experienced in real estate and an asset protection attorney aligned with your long-term goals.