However, you can look at a self directed account for your 401K or the Roth contributions. 

You don't necessarily need a w2 for active income it can also be anything else like self employment works too you just have to wait one year of tax returns but run your business for at least to years to use it and make sure you don't write off too much as you want to be able to use the income to qualify for a mortgage.

Hi David,My plan is to self manage my villa.

The main house is completed and as far as labor, I spent $40,000 on just labor and that includes everything from full gut demo to finishes.We are talking about a 4BD, 3BTH two story 2400 ft.² home with a bonus room.This was a full gut job, replaced…12 Windows (new construction)2 sliding doorsTook out all carpet throughout.Took out this ugly 2” thick tile from half of the downstairs portion.Removed popcorn throughout the entire houseTook one wall downA little framing workReplaced entry door 80” x 92”Drywall patchingSmooth drywall work50 recessed lightingAll electrical neededAll plumbing neededNew cement walkway instead of one walk to the front door I created two steps with two lights in each step.Install kitchen cabinets, excluding countertopInstall all three vanities3 bathtubs with one being a modern standalone tub in the masterAll tile work (bathroom wall & floor, kitchen backsplash)Installing of all hardware, faucets, showerheads, etcInstalled 8 single panel doors with hardwareAdding self-leveler after tearing out that thick tileNew LVP flooring throughout the entire house except bathrooms,all baseboards, trimsPainting the entire house, painting all the doors, painting the outside trim.Reframing the outside balconyReframing the fireplace to install new linear modern electrical fireplaceand they took care of the two trash bins.I mean, completely redone.The only thing that was not included in the $40,000 is landscaping, counter top cut and install and of course the ADU which I’m currently working on now.So my question for my fellow investors and contractors did I pay too much?

I have clients that like to be 100% hands off and I have others that will fly in and do their furnishing/design themselves and even some that self-manage out of state. 

Other times, capital is tied up (like 1031 funds or from a previous sale or expected bonus, or timing for w2 to season or 1099 self employed to season..) for a few months.

I didn't want to, but I am considering self-managing my newly-purchased SFR in Cleveland (I'm located in CT). 

You shouldn’t ever have to visit the property if you aren’t self managing it.

First time landlord/self-property manager here, what are my responsibilities when it comes to hiring contractors and giving/ asking for 1099s?

Please contact them as we are not allow to self promote.