So long as it immediately appraises for circa $1.3M, if you pay the $900k all cash up front, you can apply for a "Delayed Financing Exception" which should get you all your cash back (ie. 70% of appraisal) straight away. https://www.fanniemae.com/content/guide/selling/b2...From the Sellers point of view, so long as your Lender is on board, they don't REALLY care if their money is from you or your bank at closing time - they just want their money guaranteed!

BoA won't do HELOCs in rentals straight up in MI

Being honest and straight forward with friends to me is the way to go.

I can't seem to get a straight answer from several PM companies I spoke to.2.  

Basically, you take on a massive amount of extra risk, courtesy of the Ontario Govt.I would consider it to be a red flag if they suggested that the checks will come straight to you.

Some people won't accept an offer until they see that you CAN get financing. if you already have the 20-25% downpayment ready, why don't you go straight to a conventional loan?

I think the agent simply took market rent, applied them to all units, and used one of the R&M rules to come up with his number2. property manager listed no rent income for 6 months straight and suddenly for the very last month on paper there was an income of about 2800 dollars. this made me doubt if the entire income and expense reporting was accurate3. owner did not provide tax or insurance numbers - the listing agent estimated them...I also heard from the selling agent that one of the bigger units will be vacant from next month, due to eviction of tenants from rent delinquencies The owner is out of state and seems clueless on the operations of this building.

@Daniel DietzYour analysis is in the right direction, but not quite there.1) Determine the debt financing ratio - in this case .602) 60% of the gross income is then looked at by UDFI3) 60% of all deductible expenses are applied, so 60% of straight-line depreciation, 60% of the interest on the note, 60% of property taxes, etc.4) $1000 exemption applies5) The net amount after deductions and exemptions is then taxable to the IRA, and the trust tax table is used to determine the tax amount.Even if you have a negative UDFI liability, it can be worth filing the 990-T in case you can carry that loss forward to future years.We have a UDFI calculator on our website and if you PM me, I can send a link to you (BP does not want me posting that outside content on their forums).

Pretty straight forward.How can I determine if buying a condo to occupy makes sense compared to buying another investment property?  

That is what you gonna have to do just to get that first deal under your belt be straight to the point in price for both sides.