You’ll get a better return over the long-term by putting your money 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 could put most of your funds in the stock market and access them when needed for a HML.

Chicago is losing housing stock at an alarming rate. 

@Jason Sinclair, having a designer for a wife, I would answer that it really depends heavily on each house, the flow and usability of the spaces as they are, and the overall use of space in the house as a whole.That being said, while there may be a small shift towards more separated spaces, "open concept" is by no means dead, and in many markets, most people seem to still want to have connectivity between their communal spaces.In fact, my wife's current flip is a split level (although technically it is a split-foyer), and she is taking out a structural wall to connect the kitchen, dining and living areas.  

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

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.

Add a Rental Security provision to receive stock options in Lazy Dogs LLC for any upside when it goes public!

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). 

Unfortunately, I live in the dead center of it.