Some may require a waiting period of one to two years before leasing is permitted, while others may prohibit rentals entirely as outlined in their bylaws.Always know the property’s potential for annual rental income and ensure the numbers work.

I suggest the buyer at least get an estimate of the potential tax savings. 

It seems every market goes through a cycle -- unnoticed potential; early titillation as the potential becomes known; flood gates open and gold rush is on; property prices rise, revenues drop, regulations come in; and finally balance is found.

@Hector Lewis - The decision ultimately depends on your current cash reserves relative to your financial needs, as well as your willingness to reinvest for potential appreciation.

I'm an RVA native, born and raised and have had experiences that could if shared with you could potentially be a big help to you. 

It can provide a very misleading valuation.Your appreciation numbers reflect just below 4% a year (I used 8 year hold) on both properties which is below national average for this period and below what neighborhoodscout depicts for Chicago 10 year average. https://www.neighborhoodscout.com/il/chicago/real-estateLooking at this from the outside, I am missing a lot of details such as your interest rate, is there a prop tax benefit for long holds (by the way look up prop 13 for CA at some point as it may play a role in your decision to purchase once you relocate to San Diego), the neighborhood, appreciation potential going forward, any emotional attachment, etc.  

@Holly Thorsen see above for potential challenges tapping your equity in the rental.You only need 5% down for a regular mortgage, 3% down for an FHA mortgage - so why don't you have the funds?

While most of his experience is with new construction rather than remodels, he’s already given me a few pointers and is looking into potential referrals for me.

Which is very complex and costly and likely warrants professional help.Now, if it's just you and your spouse, then your 2024 tax preparation is likely relatively straightforward:- you will create a Schedule C on your personal tax return- you will NOT report any costs of purchasing the property or its rehab, not in 2024- you will report your business overhead expenses such as marketing, driving, technology etc- you will end up with a business schedule showing zero income and some expenses - not breaking the rules but potentially raising an audit flagCan you do it yourself?

I'm wondering about any potential regulations that might make this a more difficult process than I'm anticipating.