From what you’ve described, it sounds like you’re more focused on long-term appreciation and future benefits rather than immediate cash flow.

Alternatives include seller financing, a lease option, or using an LLC or trust to structure the deal while maintaining tax benefits.

If you are in a decent area where appreciation is on your side, its better to bite the bullet now, hold, and reap the benefits in the near future!

., structural updates) can be added to your basis, while maintenance costs are deductible in the year paid.Since bonus depreciation is now at 40% for 2025 and 20% for 2026 under the current law, future real estate investments will have fewer upfront depreciation benefits.

.- Cash flow vs. appreciation: If the new property is in a market with strong rent growth, you’ll benefit from increasing NOI over time.- Stock market opportunity cost: If the brokerage account has strong holdings, consider if the return potential justifies cashing out now.Given the current market dynamics and your goals, reallocating your brokerage funds into a multifamily property in Rochester could provide substantial benefits.

Paying those things benefits you because they facilitate STUFF exiting the house. 

STR seems to have better tax benefits (in the right market) but is it worth it at a distance ???

Include a buyout clause allowing you to transition to sole ownership after two years, based on a pre-determined valuation formula or market value.Use an LLC to hold the property for liability protection and pass-through taxation, ensuring both partners benefit from depreciation to offset rental income.

Quote from @Amit Chugh: @Tim Delaney - I was referring that one of the properties is listed as Section 8 Property, why one would list that in title, does it make any different or benefit for buyer or seller mentioning section 8 in title?

Forming an LLC for your rental property can offer liability protection, but no real tax benefit.