I delayed more than $60k in taxes even though I live in a state with no state income tax or it could have been closer to $90kMy TOTAL additional cost was $700 give or take.

Sometimes it’s money, sometimes it’s time, and sometimes it’s just not wanting to move their kids mid-school year.Anyone else had a moment like this, where shifting your approach unlocked better conversations?

The more you understand investors, the more opportunities you unlock.

Once you have separate APNs and condo titles, you unlock conventional financing and a broader buyer pool.

Setting up the right entity (LLC with possible S-Corp election) can help reduce self-employment tax exposure.Long-term rentals reintroduce passive activity rules, but combining them with STRs or qualifying as a real estate professional in the future can unlock additional tax strategies.Regardless of the path, detailed recordkeeping of travel, supplies, contractor payments, and property expenses will be critical to maximize deductions and defend them in an audit.Starting with STRs is a strong move because the tax code gives you more flexibility to use losses and deductions against your active contractor income while you build equity.

There could be a potential opportunity to aggregate the bar and the property as a self-rental which could unlock some potential deductions 

I’d rather own fewer, better-located houses that lease early and renew cleanly than chase C product that steals my calendar.3) Renewals (incentives > flat fees)This is a big unlock.

That’s why many people refer to it as a “loophole.”With long-term rentals, you normally need REPS to unlock that benefit, and even then there are income limits that can phase out losses.

I am currently paying additional principal ($4000-5000 per month) spread out to most of the properties but was wondering if it will be better to apply all of the additional payments to one of the house pay it off and then move to another house?

I would recommend starting by meeting a local lender or small community bank for a cash-out refi or HELOC on the $260k property to unlock equity for the next purchase.