the lender that did your last loan is  likely  afraid of  facing an " EPO"   ( early payoff penalty )   which would require them to payback any rebate they earned  when they closed your last loan  ...most loan programs  have this  stipulation and these tend to  fall off at the magical 6 month mark 

I take an honest look at what the building can support, give an extra margin of safety, and take out about that much. 

If the bidding type includes a premium, you need to learn the statutes/rules to see if the premium is paid back (sometimes yes, sometimes no) and if the premium earns interest (sometimes yes, sometimes no). 

My long-term goal is to exceed and eventually supplant my current projected earned wage (about $100k annually).Purpose of financing: to purchase the above mentioned property Type of financing sought: thus far, it seems like I'm restricted to a few options:1.

I think part of the reason I want to be licensed is to earn the commission a realtor gains from buying/selling property.

Money received is never “tax deductible”....points would be earned interest income.  

I would update your lease to include fines after an initial warning about leaving trash or personal items in the common space.I wouldn't allow tenants to mail in the rent.I allow them to deposit directly into my account, ACH or Zelle.Maybe get extra trash cans so that they don't have to leave their bagged trash by a full can.

@Ryan McGrath I think your first concern is to make sure it's a legal rooming house or to understand the steps that it will take to make it one - which I'll bet would include things like extra egresses and a sprinkler system.One incident / phone call / police visit where word gets back to the building inspector and you might find a big red "VIOLATION" sticker on your front door.Next, I'd want to do some forensic accounting. 

I don't know what they meant... but you can contribute to an IRA from your earned income.

It took 1 year to get all of the offices and the 7 extra parking spaces leased out, but now it cash flows beautifully.