I have a RE LLC with each property in an RPT.I own 3 LTR SFHs in North FL that I acquired pre/during-COVID.

Here’s the kicker; you and sis have to convince the three of you that the places you want to acquire meet that model, and let dad critique your proposals.

This could also be a good opportunity for that 1031 exchange mentioned in your original post (since it doesn't sound like the timing may be 100% for the primary residence exclusion), but only if you want to acquire a similar rental/investment property.

Because he/she will know the process of buying / selling properties so they can be better suited to ask you the right questions.For example, since I acquired properties in the past, I know the ask clients if they got a home inspection/appraisal / survey prior to closing on the property.

When it comes to acquiring lucrative coastal luxury vacation rentals on the Oregon Coast the most challenging components can be permitting and timing. 

The answer will depend on how you and your partner acquired the property.Did you acquire the property as tenants in common or through an entity?

Acquire enough RE that it takes you or your spouse more than 750 hours a year and 1/2 of your time to manage.When you are a material participating RE pro all of your and your spouses’ RE activity becomes active, allowing you to offset RE losses against other active income.One pitfall of a RE Pro spouse if you are full-time W-2.

Plus, if you continue to acquire more properties, you’ll have a solid, legally sound lease to use without having to worry about your license being in jeopardy.Good luck with your new venture!

If a property has existing renters are what are key questions or top of mind items to be thinking about when acquiring the property with existing renters?

The two earliest popular and successful “gurus” were Jimmy Napier, whose speciality was investing in notes, mobile homes, and real estate “exchanging”, and John Beck, whose speciality was tax auctions, and complex series of exchanges in which John used near worthless lots acquired for pennies at tax auctions at full tax assessed value for exchange purposes, usually as a downpayment, or as collateral for a private note.