$40 - $50k each would be a low annual average. 

.** Slight bias against Florida due to anticipated stress and anxiety of watching a hurricane hit your vacation home annually, ha.

You said a “little” money, so bear in mind if you transfer that into a self directed account the annual contribution limits are $7k plus $1000 catch up over 50 so it may take a while to get it to a point where you have enough to invest in real estate.  

.,   What kind of annual ROI is usually typical in a syndication deal?

The city is one that’s consistently listed as a top 10 2024 real estate market, the projected cash flow is intriguing ($50,000 - 25% down payment, estimated $7500 annual cash flow), both units are leased until October and December (as a potential new landlord this gives me some security), but I feel hesitant with offering on a century old property.

I'm drafting the legal documents myself so that saves.Maintenance will likely be about $300 annually for filing fees.

Only problem is with a short term my monthly mortgage payment will be 2K, and will cut deep into my cashflow during that time.With a little work I can get my COC to 3.1% per month for that 12 years.Appreciation is about average in this area and I expect to get about 4% annually maybe 5%. 

When I did I can leave it to anyone tax free  and then they will get $20k/mo plus annual increases for the rest of their life.

After growing up on the lake and nearly a year of real estate research here is what I can tell you:There are pros and cons right now in Branson related to STR:Pros:  -Branson is popular and growing in popularity - approximately 8 million visitors annually for a city of 10k population is pretty massive-Peak season is definitely the summer months, but even September-December do relatively well from a tourist standpoint. 

20-30% annualized returns for passive investors for a commercial development deal is common...and required to offset the related risks.