Season the property for 3-4 months, then do a 65-75% Cash-out ReFi. 

Also after 2019 tax season I will have two years of self employment to include on future loans.

I know that peak rental season is during summer, and most lease are one year long. 

There’s no problem anticipating that rentals will provide for your family there’s 3 things to consider:1) legally set up operations so that your beneficiaries can simply continue them without any kind of weight of going through probate (other wise a little life insurance for probate season can be helpful- this should really be a conversation with your lawyer if you have questions about probate - thankfully @Pat L.’s doing the right thing with the trust).

A property will need to season 6 months from point of purchase in order to get a traditional loan if you are considering to get cash out.There is always a risk that a lender can call the note due in you add it to an LLC but that's a limited risk. 

Someone below or above in a thread mentioned they were lucky enough to get on a call from a seasoned investor.

I then put in the pricing for on season off season etc and let Excel give me an average price.

The only people who should & do profit in neighborhoods like this are seasoned, grizzled battle tested veterans.

I worked my *** off to own a firm so I could take 3 days off during tax seasons if I wanted to. 

(This does not apply to two or three-family owner occupied dwellings, motels, hotels, transients or seasonal tenants). 2) The new lease terms (1 year lease, rent increase per rent control, no subletting).