My cost basis for my properties are consistently off from my tax returns because Stessa will include everything in the basis even though it shouldn't be.  

We are in Tampa so a similar market.We provide a starter set which is clearly communicated to guests (thought some people do not like it and clearly do not read which you cannot help) generally consisting of:- 2 Laundry Pods- 2 Dishwasher pods- 2 Rolls of Toilet Paper per bathroom- 2 Paper Towel Rolls- 2 Trashbags- All soaps are refillable including dish soap, hand soap, and body washes/shampoos.They are expected to get their own should they run out of anything. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

@Pat Aboukhaled I would ULS (unit lot segment) the primary house and include a clause in the call option that would prevent them acquiring the DADU.

Pairing that with relationship-building will help you uncover off-market opportunities and find local experts who can guide you.For meetups, here are a few ideas:Indianapolis Real Estate Investors Association (Indy REIA): They have a mix of virtual and in-person events and are a good starting point for networking with other investors in the Indy market.Louisville Real Estate Investors Group (REIG): A similar organization for the Louisville market, with educational and networking opportunities.Check out BiggerPockets Meetups: Many cities have local meetups organized by investors active on BiggerPockets, and they often include virtual options.Facebook Groups: Look for local investing groups like "Indianapolis Real Estate Investors" or "Louisville REI."

This would include adding another bedroom and making it a full 2 bath.

Also, SAAS platforms are supposed to include support and service (that's the last S), but the quality varies greatly from company to company. 

. $69k for a 3 unit with gross rents of $2k a month and total expenses of $800 a month which included management and capX.

Regarding the condo/townhome situation in Fort Myers vs Bonita Springs, I would say the more important things to focus on would be the association fees charged, what is included in those, and the rental restrictions of the association.

Or the listing agent includes it in the property info on their website, or shares it when a showing is scheduled.