This initial negative equity position consumes the initial cash flow.  2) the addition of the adu makes the property multi family and likely makes rent control apply.  

In addition to conventional loans and FHA loans, if either you or your wife are veterans, the VA also has a rehab program.I'd be happy to discuss my rehab experience both as an investor and as a mortgage broker, and at least help you think through your options. 

This was not what I was interested in doing and when I voiced that I was interested in 5-20 unit deals and had the funding for that in place I just got additional push back for buying the larger buildings.

In both you are now paying taxes on an additional $1K/mo.

Additionally, would love to hear how others manage multiple listings with the help of others.

Every property i use it i make additional tweaks.  

Additionally, the Villages are close by and with an aging population it attracts a lot of healthcare field workers.Now, with a lot of rental properties you may run into slightly longer vacancy periods if you have a unit turn at the same time as others, but generally speaking renter demand is solid. 

Does anyone know a property manager that supports small self-storage rentals in addition to residential rentals?

Most lenders who order appraisals are required to order them through a 3rd party AMC, which can add additional costs to the appraisal but ensures that there is no lender (Or borrower) bias in regards to the values.

By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!