Quote from @Simon Walker: Quote from @Andrew Syrios: Could you "split the difference" so to speak and go back to work for yourself but limit the number of clients you take on so you only need to work 20 or so hours a week?

A 1031 exchange doesn’t apply, but funding through a self-directed IRA can defer taxes, though profits from debt financing may trigger UBIT.To reduce taxes, consider forming an LLC for better expense deductions, offsetting gains with investment losses, or holding the property for 12+ months to qualify for lower long-term capital gains rates.This post does not create a CPA-Client relationship.

If they work independently, set their schedule, and use their resources, they might qualify as a 1099 contractor, but misclassification risks IRS penalties.Wages for W-2 employees and payments to 1099 contractors are both deductible business expenses, but compliance is key.This post does not create a CPA-Client relationship.

For every angry client we have many more that are doing just fine!

Assuming you are both working and the rentals are long-term, rental losses up to $25,000 can offset W-2 income if your MAGI is under $150,000, with excess losses carried forward.This post does not create a CPA-Client relationship.

A client of mine in Maryland added smart home features to their rentals and boosted rents by 12% with minimal investment.

I've seen clients just opt to build an ADU rather than go forward with a full lot split for several reasons. 1.

That's what separates the best real estate agents who represent investor/developer clients.

Your brokerage is required to supervise you, and maintain all records of the transaction, just like any other client. 

I'd be looking at multiple structures. we try to build below the average new build cost in our market in Columbus Ohio which is 515,000 last year and we target land 40-50k and urban core adjacent where we get higher price per square foot. we build for clients with margin around $190 a sq ft depending on multi or single. we can get that down in our triplex it's a little higher on our single family homes because of garages and limited economies of scale. hope that helps. idk Philly but if you show me the area and styles of homes I can give you some more insights.