The forms are online, and it costs $100 per filing. 

Have these guys ever heard of Quicken or any of the online personal finance programs available to track spending?

It would be good to talk to a lender to make a game plan and review your financials. 

Hi Thanh - Managing a single STR can be manageable, but as your portfolio grows, hiring a vacation rental company can be a game-changer.

Online payment. 

If you're looking to buy bigger buildings that's another ball game altogether.My advice: what investing do you feel most confident and excited about?

STRs are also not my game and I prefer to stick with what I know. 

These are features like online renter payments, tenant portal (for payments and work orders), help keeping track of work orders, tax reporting features, and accounting functionality.

You may be able to see if a retailer still sells the 2024 version.If you can't get the one time purchase, you would need to see if the cost is beneficial.For real estate -  Quickbooks desktop > Quickbooks online because you can set up multiple entities within quickbooks desktop and not pay an additional cost per entity that Quickbooks online would charge you.Best of luck! 

G'Day Alejandro,As a few have already mentioned, take a peak at Toledo also.In my opinion lower potential for long term appreciation but solid/"boring" cashflow.I prefer my portfolio to be "boring" but cashflowing lolLow entry points (Sub $100,000), high rents (Above the 1% rule).Blue collar working class decent folks that will stay and pay.Depending on the area but no derelict homes, yards well kept, cars with wheels and all tenants are employed.Plus, all are sophisticated enough to pay rent online so property management doesn't have to collect rents with bullet proof vests and shot guns lolI'm bias toward Toledo but it's worth considering.Wishing you much success