Your broker may have forgotten, but when the appraiser reports back to the lender that it is a rooming house, the lender will walk away or only underwrite an LTV of 50-65%.Your best bet is either a private lender or finding a conventional lender which uses auto-approval software (TD is an example) and mortgage agent/broker who can steer you towards an application that qualifies for auto-approval (if at all possible).When we were first in the same situation, we approached a family member with a proposal to have their name on title and live in the house (rent and utilities free) in exchange for their serving as the Den Mother to keep the house in order.  

When I am looking for renters and doing the application process, am I required to send letters to the applicants that I am not renting to with a reason.

There are also some software and Apps that do a lot to automate the management aspect as you continue to scale.Collin

The only problem is that I have a misdemeanor petty theft from 10 years ago on my record and I know that can be a reason for the board to deny my license application.

It takes time to build a pipeline so the right individual would need to be willing to spend this time learning the process and executing practical application.

Additionally, you have many structures that could be applicable depending on the asset. 

RR You might be surprised how deeply offended folks can get when you suggest dropping a spouse from the mortgage application to get a better rate, lower fees, or to get it done at all. 

Switch your mentality and when you hear them put you down, understand 1) they care about you, 2) they’re speaking from their experience and your results will differ greatly based on your application of this education, 3) All successful people go through this.

@Dewayne C.Quickbooks desktop version should be able to handle the bookkeeping function that you are looking to have done.If you are looking for a tax-software to self-prepare your return, any software should be able to handle it so long as they provide Schedule E in the package.Alternatively, you may want to work with an accountant to handle the back-end while you work on making more connections and analyzing more deals.

A couple filled out application for renting my property.