Learn the system that all people, accountants, CPAs and all are going to use which is quickbooks so you know it and it can be transferred easy when you are ready to move from self managing to bookkeeper to accountant. 

Some guests may not mind minor disruptions if they know in advance.From a tax perspective, turning the main house into a short-term rental before selling could be a good move, it allows you to claim bonus depreciation and other STR deductions if you materially participate.

I’ve heard with quickbooks, since I’m doing a brokerage but also 12 separate houses, is with rentals each one is a license, etc. 

The LLC when operated correctly separates business liabilities from personal assets (exception usually being the personal guarantee on loans).

If a single-family has a basement that could be converted, I’d only move forward if it can be a legal, code-compliant second unit - egress, fire separation, ceiling height, parking, permits, the whole nine.

Sometimes when people actually model the gain, the “$266K for taxes” number moves a bit — better to find that out before you start investing the rest.

If the property qualifies as a separate activity, you may be eligible to claim bonus depreciation through a cost segregation study, which can provide substantial upfront deductions — particularly beneficial if you are in a higher tax bracket.However, if your income level is lower, the cost of the study may outweigh the benefit.

We have not ironed out any details yet but we will put together a joint venture agreement ahead of moving forward with any deals.

Quote from @Mary Jay: @Mary Jay While I can’t tell you exactly how much your tax will be, I can help clarify how the gain is generally calculated.When you sell a rental property, your taxable gain is based on the difference between your sale price and your adjusted basis; not on how much you owe on the mortgages.Your adjusted basis starts with your purchase price, plus certain closing costs (if they weren’t deducted previously), plus the cost of any capital improvements you’ve made over the years (like renovations or additions).The gain is your sale price minus that adjusted basis.From that gain, you’ll also have depreciation recapture, meaning the total depreciation you’ve taken (or should have taken) while the property was a rental is taxed separately.

They built the house in anticipation of moving and then decided not to.