@Jeff ShaverIt's good to see a fellow San Diegan on here.If your goal is higher monthly cash flow, transitioning to larger assets with better economies of scale (like multifamily) could make sense.

I’ve experienced success in the STR market here in St Pete myself but I’ve since transitioned my properties to long term rentals for convenience and time management sake.

Hi BP Community,I’m a multifamily investor based in NJ, transitioning from smaller multifamily units to 6+ unit properties.

Once that phase is complete, I’d transition back into long-term holds.As for the cash-out refi, without at least doubling the rent, I’d be in a net-negative position each month, which doesn’t seem like a worthwhile trade-off.On the tenant side, I agree with your point about the business aspect—it’s something I’m working on coming to terms with.

With your experience and a clear goal to build wealth and transition into multifamily commercial properties, you're on the right path.

If you are still with CR of Maryland they will transition you to their management system. 

Keep in mind all these markets are very different than the Cambridge area in terms of tenant base, household income, transit, etc.Happy to connect if you'd like to chat more!

I could see really getting into this and wanting to keep growing the number of properties I own so long as I can keep qualifying for loans, so I need to understand how to transition away from the VA loans once I'm maxed entitlement and keep growing my portfolio.So it's build up equity then huh, and refinance out of the VA loan or cashout to buy on another loan type?

While cohosting is my initial step, my goal is to transition into a full-service hospitality management company as the business grows.

After discussing with Justin, I am certain that we can help you in your scenario as you and your wife transition from one industry into more real estate.