I want to be sure it's the right time when I transition from research to getting the ball rolling.Thanks - looking forward to hearing from y'all.

Stock the unit well, make check-in smooth, and go the extra mile with amenities.With a few of these strategies, your parents should start seeing some positive traction.

There will be MANY times where things do not work out in your favor and most of the time things don't work simply or smoothly BUT over the long haul its worthwhile.

Make sure you’re working with a lender who has experience with 203(k) loans and a contractor who understands the program’s requirements.2.Loan Process Can Be Slow – Unlike a standard mortgage, the lender will be heavily involved in the renovation funds, which means more paperwork and potential delays.3.Strict Repair Guidelines – The work has to improve the home’s safety and livability, so luxury upgrades usually don’t qualify.4.Living Through Renovations – If you go with a Limited 203(k) (up to $35K in repairs), it’s usually manageable, but for a Standard 203(k), major work might require you to live elsewhere for a bit.It’s a solid strategy, just make sure you’re working with the right lender and contractor so things go smoothly.

@Nicholas Sanchez Yes, you're on the right track—working with both a real estate attorney and a tax-focused CPA is exactly what seasoned investors do when transitioning from house hacking to building a structured rental portfolio.

Is it hard to transition from that structure once you are a more advanced/seasoned investor? 

May 2025 Coachella Valley Market ForecastMarket Insight – Based on April 2025 DataMarket Momentum Shifts — Inventory Is Up, So Are Pending SalesApril data revealed a meaningful shift in the Coachella Valley housing market:Active listings increased to 3,706, the highest level in over a year.Pending sales also climbed to 975, marking a 14-month high.New listings, however, dropped to 1,205, indicating that while supply is elevated, seller activity may be slowing.This suggests a transitional market: buyers are active but selective, and overpriced inventory is being left behind.Months of Inventory: Supply Absorption Is ImprovingThe market peaked at 6.3 months of inventory in October 2024.That figure is now down to 3.8 months, based on pended sales.This indicates healthier demand, especially when viewed through a seasonal lens.

That kind of background makes a big difference when transitioning into LTR or hybrid strategies.I'm Kyle Morrison, based out of Ocala—I work in real estate and property management here, and I’ve been seeing more and more people look at creative setups like the one you’re describing: something multi-family, ideally with a space to use personally part of the year, while long-term tenants help carry the mortgage.

Love the transition from automotive to tech and now real estate! 

Somerville’s high studio rents ($2,000+/month) often justify the investment, but run a pro forma to confirm ROI.Parking and Other Rules: Check if Somerville requires off-street parking for a new unit, though exemptions may apply near transit.