Readers should seek professional advice.

Unsolicited advice to any young professionals just starting their career.

@Greg Seivert You're absolutely right to question that advice.Just because you qualify as a Real Estate Professional (REPS) under IRC §469(c)(7) does not mean your rental income shifts to Schedule C, and it does not trigger self-employment (SE) tax.Rental income, even when you're a REPis still reported on Schedule E, unless you're:Providing substantial services (e.g., cleaning, concierge, hotel-like operations), orRunning a business like flipping or wholesalingREPS simply allows rental losses to be treated as non-passive, so they can offset other income like W-2 or business profits.

@Matthew Montanarella              "How can I best prepare myself the next 24 months to be ready"Network with other investors and professionals that you will need to work with, lenders in particular.

.), you're often limited to $25,000 of passive losses per year—and that phases out completely if your modified adjusted gross income (MAGI) exceeds $150,000.Real Estate Professional Status (REPS) or the STR Loophole: To use rental losses to offset W-2 or other active income, you must either:Qualify as a Real Estate Professional (750+ hours, primarily in real estate) and materially participate in the property.Or, if it's a short-term rental (average stay under 7 days), materially participate (100+ hours and more than anyone else) to convert it from passive to non-passive—even without REPS.Standard deduction vs. itemizing: You mentioned your CPA said deductions didn’t help due to the standard deduction.

If you’re seeking financing that range is typical unless you're bringing in an equity partner.You might consider structuring this as a joint venture with someone who brings capital and shares in the upside, especially if you’re open to giving up some equity in exchange for more reasonable termss 

He has identified this helps him legally when going to court seeking Use and Occpancy fees. does this type of strategy work in other states?

Seeking Advice: Best Investment Markets Near Boston (<$1.5M, Lakefront Properties)Location: Massachusetts (Greater Boston Area)Investment Strategy: Buy & Hold / Short-Term RentalBudget: Under $1.5MHey BP Community!

Quote from @Val Sundberg: What’s the biggest challenge you face when seeking private money lending for your real estate projects? 

Readers should seek professional advice.