I was also considering the REI expo in February so maybe I'll see you there.You're a self-proclaimed novice but I think many other members of the community would agree that you're well on your way given your potential cashflowing rental and equity.You seem to have a strong position which would allow you to keep growing your portfolio in the next few years.I'd recommend diversifying your RE portfolio the same way you're diversifying with other investments (REITs, Stocks, bonds etc.).

sell third house this time dump half the profit into SnP 500 index fund, other half builds fourth house... repeat until satisfied with stock portfolio, retire at 50option C) Aggressive model: sell house for $600k just keep carrying my primary mortgage which is $2900/month and dump the money into 2 properties and build 2 house at once that would each be worth $600k...?  

Just remember, Real Estate is a long term investment and you are ultimately enjoying the appreciation and principle reduction. 

With a HELOC being around 9% I'd probably be paying more in interest than the money would make in the stock market.

Some design and amenity ideas:+ Welcoming living space with plush seating for family hangouts+ Coffee bar or stocked tea station for early mornings before campus events+ Dining table or breakfast nook perfect for family meals+ Dedicated workspace for parents who need to check in on workFor sports fans, tap into their game-day energy and make your STR the go-to spot for a fun, convenient stay:+ Big, comfortable seating & a great TV setup (think oversized couch, streaming sports channels)+ Game-day essentials like a mini fridge stocked with game-day snacks/drinks+ Outdoor space with a grill & seating for pre- or post-game gatherings+ Good parking (sports fans hate scrambling)+ Team spirit decor touches (subtle, not tacky—think framed sports prints, not full-on mascot murals)Your design & reviews will do most of the marketing but to market directly to these guests:🎯 List your STR on sites where parents and alumni book (if allowed)🎯 Partner with local businesses—coffee shops, sports bars, or tailgate services—where your ideal guests hang out🎯 Optimize your listing title and description with phrases like “Perfect for Visiting Parents & College Game Days”🎯 Time any discounts/promotions around major campus events—homecoming, graduation, big rivalry gamesThink of it this way, you’re not just offering a place to stay—you’re creating an experience they’ll want to book again and again.

You might find that the stock market makes you more money with less work (seems you are trying to minimize your involvement w/ the rentals). 

More effort should go into enforcing existing permitting laws and cracking down on unpermitted work rather than imposing costly regulations that push property owners into avoidance tactics.If the goal is to improve fire safety in Worcester’s aging multifamily housing stock, the best approach is to encourage full renovations that bring buildings up to modern safety standards—not to place additional financial burdens on responsible owners.

The 25k would do fine in a stock index that suits your risk tolerance.

There are four key principles that guide me:- Consistency is everything- Never stop learning- Take Action- Value relationships over everything else1) Consistency is everything There are multiple things that I do every single day- Read – 10+ minutes.

The principles in the Academy are aligned but what sets it apart is that with Nate it's a more granular level.