Hi - congrats on purchase, Championsgate is a great STR area, as somebody who owns and manages homes in the area, I would suggest you use a STR broker, Fudge insurance are in Orlando and specialize in STR homeowner insurance, we use them for both our properties, but also other insurance needs.

Good luck  Total Rents Collected: $23,025/mo Debt Service: $12,358/mo (sad for me. 8% interest rates lol) Property Management 10%: $2,303/moReserves (Vacancy 5%, Maintenance 10%): $3,454/moPhantom Cash Flow: $8,365/moTrue Cash Flow: $4,911/mo (Money I can legit burn)  bob as you probably know I owned a few hundred of these types of homes from DetroitCleveland to Jackson ms  Birmingham balt city etc etc.  

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.

Self-Employment Opportunities: Would it make sense to start a side business related to my rental properties (such as property management) to access more deductions?

What percentage of gross revenue does an owner typically keep if they do employ a property manager?

Cash flow depends on the down payment, but using a HELOC could keep your cash reserves intact while you get started.Make sure to build a reliable team (property managers, agents, etc.) to help you manage the property while working full-time. 

Private lenders or even creating a small syndicate with a group of investors might also be worth exploring, especially since you can point to your uncle’s track record and your own experience managing rentals as a selling point.If timing is tight, you could look into a bridge loan to secure the property while figuring out a more permanent solution.

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.

I am currently a sales manager for a commercial tree farm and have recently been consuming Kiyosaki's books like they are candy.

However, there's a critical detail that many tax advisors conveniently overlook when promoting these studies.Here's the uncomfortable truth: If you're a high-income earner (AGI > $150,000) and not actively managing your properties, those promised tax savings might be locked away for years.