The small multi space in expensive markets can be a weird no-man’s land.Here’s the framework I use when choosing between the two:If the SFH rents at a stronger price-to-cost ratio than a duplex, and leases faster with a stickier tenant base, SFH wins every time.If the small multi gives you true economies of scale (shared utilities, lower taxes per door, strong rental demand), then the multi wins.In many Florida submarkets, SFH simply has the advantage.If your long-term goal is to replace your W2, the most important thing is buying into the product type that actually rents fast and stays full in your market.

A few frameworks investors use in your situation:  Start with a BRRRR using your $100K Low risk, lets you learn the process without touching your home equity yet.

As a smaller, self-managed landlord I think solutions that offer that kind of scheduling/logistics framework are solving for one of the most long-standing self-managed challenges we've had for years: how to scale and systematize operations when you're are landlord or PM out there hustling for your next deal. 

Coach house > garden unit from a lender’s perspective every time.You already called it out, but it’s worth emphasizing:Garden unit = discount, scrutiny, sometimes zero usable incomeCoach house = fully counted, sometimes even a positive factor in underwritingIf your plan is to rinse and repeat loans, this matters a lot.My take:If the Jefferson Park asset looks solid in person, I’d go that direction.It lines up with your actual stated objective: scalability.If it ends up being mediocre or has big CapEx concerns, then the West Town deal becomes the better long-term hold, but with the understanding that it might slow your next purchase.Either way, you’re clearly evaluating these with the right framework.

It is normal to admit to the alienation you may feel to the dynamic and changing marketplace especially if you have spent decades mastering older more traditional frameworks which are no longer relevant.

Without the right legal framework, both personal and business assets could be vulnerable.

Alicia, your logic is on the right track, but here’s the clearer framework so you don’t accidentally miss or misinterpret the rules.1.

That part is not complicated and not optional.Second, state rules.Every state has its own framework.

(Willful violations of the Truth in Lending Act (TILA), which is part of the Dodd-Frank framework, can result in criminal penalties including a fine of up to$5,000, imprisonment for up to one year, or both.)Capex is indeed a problem; investors usually "budget 5% which comes out to $75 per months, $900 per year.

Be sure to review your state laws to determine whether entity grouping is permitted—grouping may be allowed, but each LLC would still remain a distinct legal entity.For ownership structure, you may add a partner or operate as a sole proprietor within the LLC framework; however, I do not recommend using an S corporation for real estate properties.