The key would be to properly line up a plan (Scope of work, contractor, exit numbers)!

I completely get where you're coming from; the fear of starting can be daunting, but the rewards of pushing through that fear are immense.I’m involved in real estate investing, specifically focused on new construction duplexes in Indianapolis.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

Otherwise it sounds like you've got a great plan!

Be aware Sarasota county has a 30 day minimum on rentals except some specific areas like Siesta Key.

I’m unsure how to search that specifically on bigger pockets if possible. 

@Robert Rixer, I don't know how creative these are, as many are common plays:Valet TrashFencing in first floor yardsProviding washer and dryers for added rentReserved, Covered parkingTech PackagesInternet and Cable contracts, with reimbursementsPayment Plan rents, with small service charge (i.e. bill 1/4 rent each week)Reserved Rental cabanas at poolPrivate pool party rental optionGolf Simulator in clubhouse - fee basedOn site, self serve car wash (quarter feeder style)Charged group fitness/personal training servicesGame room in clubhouse with monthly subscription for tenants (Xbox, Playstation, etc)Changing out high maintenance grass for astro turf or lower maintenance/lower water use shrubberyBut ultimately, I think a lot of NOI increases come from deep dive into understanding EVERY expense and finding ways to minimize them, and/or no outsource them.Train maintenance team on basic HVAC and appliance repairs (find way to get them licensed as needed)Buy paint sprayers for faster, easier turns versus having to hire a contract painter, and possibly repaint whole unit each timeStandardize all finishes, so you can buy in bulk, everything from hinges and door knobs to cabinets, paint colors, and light fixtures.Potentially get leasing people onto lower base salary with higher bonus potentialBulk/bundled insurance across portfolio (even better at scale is to self insure)Regularly test sprinkler systems for leaks.Non-NOI, but benefit to you: partner with insurance agency to get referral kickbacks from your tenant base for renter insurance.  

Growing out from my CT portfolio to MA specifically Pittsfield.

I need to just to plan accordingly. 

Thanks,Hey Joel,If you are tight on PITI, then I usually recommend looking into an interest only loan, maybe on a 5-10 year IO plan, to lower your payment and see if you can squeeze it in.Plus, rates are starting to dip a little bit, so it makes it a little more doable, especially if you just do a rate and term refinance to help keep your rate lower.