@Eric B. You are in a good position, for sure. I have to say I resonate with so much of how you have described yourself. I am a fail-forward kind of person and also get very hyper-focused on a subject when that subject has gotten my attention.
I will give you my thoughts on how to make that money work for you here in VB in different ways, and I will try to take into account your goal of being able to walk away from your job if it ever comes to that.
LTR: Hampton Roads is a relatively expensive market, and with that market, LTR opportunities that pencil can be few and far between. I would suggest looking into the Norfolk area or, specifically, the neighborhood of Green Run in VB (I own an LTR there and just got a buyer from here on BP an LTR in this neighborhood.). The margins are slim, though. The price point that tends to work best in this area is in the low 300s, and with the 100k a year, you could probably pick up 1 LTR that cashflows a couple hundred a month each year. Do that for 5 - 10 years, and you will have an abundance of equity and plenty of cash flow. Better yet, find some that need work, do two deals a year with renovations, and increase your velocity of money.
MTR: I would target properties that can still break even as LTR, so you have a fallback but some flexibility to go a little nicer on finishes. Like someone else already said, you are getting into a little more work for yourself, and you need to be more nuanced in your setup to attract the perfect tenants. You could still acquire one property per year and furnish with the 100k, but your cash flow should be that much higher because it's MTR. You will need to be pickier on location, trying to target areas that need the housing for Nurses.
STR: This is where things change a fair bit. The first thing you need to know is the local restrictions. Norfolk is not too bad on restrictions. You just have to avoid homes that are on the flight path of the airports. VB is fairly strict on STRs. There are currently only two areas that allow STRs. The Resort District is right at the end of the 264 corridor, where the bulk of the hotels are located on the Atlantic Ocean. The second is Sandbridge, which actually made Vacasa's top 5 list for 2023. The downside here is the price. Sandbridge median price is in the 900k range. The revenue on well-run STRs is also very high, well into the 100k+ range. With this strategy, you could combine the 165k from your home sale and the first year of 100k into an STR in this area, and you should be able to cash flow nicely. You get the advantage of appreciation on a much higher-priced asset as well as the cash flow. Then you take a similar approach and reinvest the money into more STRs along with the 100k a year, and you could have a couple of beach homes that are all bringing in six figures after 5-10 years. There are also other options to STR in the surrounding areas within 2-3hrs of Hampton roads.
I know this was a lot of information, and I hope it helped a little bit to visualize what each strategy could look like in this area. There are a million other ways to skin the cat, and I would be more than happy to discuss those over a coffee or a beer when you get here to the 757.
