When I'm looking at potential opportunity, price isn't that big of a factor.

Nonetheless, I am not out to impugn anyone's intentions and I do understand (as Jay rightfully points out) that the self-employed (my situation for the past 20 years) especially run into times in their lives when conventional lending sources are of no use due to limited reportable income and other factors (such as when, for example, you retire in your 50's and begin to live off of your lines of credit, etc.). 

If you’re looking at retrofitting to separate heating for each unit (like furnaces or mini-splits), you might be looking at a higher upfront cost, but it can shift utility expenses to tenants and improve your NOI.I’d factor in boiler age and efficiency when analyzing deals and if it’s near the end of its life, negotiate a price reduction or a credit.

Here is some key information:Property recently hit the market and has 2 cash offers alreadyThe seller provided a pre-inspection report, which I shared with 2 different lenders, both think it may fail conventional financing due to potential structural and electrical issues (realtor thinks it could pass conventional)Seller has 100% equity but is behind on other payments (not sure of the urgency money is needed)This is my first attempt at an “investment” property so I’m new to thisI see 3 optionsMove forward with an offer using conventional loan pre-qualification-Not as attractive of an offer to the seller-Possibility that appraiser calls out structural/electrical issues that need to be fixed before closing, effectively causing financing to fail- Best terms and fewest loan fees for meUse a rehab style loan such as ChoiceRenovation-Even less attractive than a conventional offer to seller, but less risk of failed financing if appraiser calls out issues-Slightly worse fees and interest rates compared to conventional-Lenders tell me possibly up to 60-90 days closing in some cases, with red-tape for contractor requirements and draw schedules (sounds like the most hoops to jump through during rehab)Use a hard money lender-Most attractive loan option I can give to seller so I can compete-Much higher fees and interest rate for me-need to refinance into a conventional at the end of rehab (not familiar with seasoning periods but I think this is a factor as well)Which option would you do?

Typically, we see anywhere from $600 to over $1000 per unit (maintenance and turn costs)  depending on these factors. 

They’ve been around forever and have a great reputation for handling self-directed retirement accounts.What I like about them is that they offer both custodial and admin services, so you can keep everything in one place instead of jumping around!

My contractor has gotten impatient waiting for him and has started taking matters into his own hands (he did the jack hammering of the floors which my plumber said had "complications" and would "take forever to get through"). 

As such, just upkeep and maintenance of the yard became a factor in deciding to sell.

I just wanted to make sure there wasn’t a limiting factor of showings or interest.

Lots of factors in every location.