This conversion was done without proper permitting and approvals from the city and obviously the additional bedrooms are not showing in the county records.

In addition, if you chat with an attorney, you can start to get yourself familiar with the rental laws now, before you come upon a situation where you need to know where you legally stand and what your rights are as a landlord.

Because in addition to the less stringent seasoning requirements, a lot of these local banks will allow you to put the loan under an LLC name, and you give an unlimited personal guarantee (also known as a contingent liability). 

Additionally, because I am recently a 1099 employee, I don't qualify for conventional mortgages or FHA loans, so the appeal of house hacking isn't as applicable here.

In addition to running the screening report, on your online application request previous landlord's phone numbers as well as their number for their place of employment.

If you need additional resources, please let me know.

It literally takes an additional 5 secs to email the created invoice to the tenants. 

If the partners agree to specially allocate one item (for example, capital gains) 80/20 for economic purposes per SEE safe harbor, the corresponding tax amounts must also be allocated 80/20.However, IRS has a framework that can reallocate the partnership items based on the “ partner's interest in the partnership” if IRS determines the method of sharing the partnership items lacks the “Substantial Economic effect” (SEE) To meet the SEE, there are strict rules to maintain meaningful capital accounts including Deficit Makeup Requirement for those accounts.With the requirement, the partner must at some point contribute sufficient capital to eliminate the deficit, and the partner has the burden of the loss that partnership has and the allocation of the partnership will be respected by the IRS.This is a very high-level summary of the rules and is not comprehensive. there are many exceptions as well.Since the substantial economic effect, safe harbor allocation rules are complex and requires considerable additional recordkeeping, it's easier to follow PIP standard. 

The house also had an addition added on in the 1820's.

Also from what I understand the building department is backed up unless you hire an expediter, so another 6 months for plans and permits or additional 3k I believe