The third unit has a long term (4+ years from what I understand) section 8 tenant paying lower than market rate rent with all utilities paid by the owner.

I believe it tends to give me a slightly lower return, because the sponsor is going to be more careful, and if there is a severe downturn will prevent me from taking catastrophic losses.

This usually has lower interest than a HELOC.The conventional loan may suit you just fine, but being able to make a cash offer can give the opportunity of buying at lower price point and avoiding some of the closing costs that come with financing and underwriting.

Among the benefits of this are:1) you can claim the deduction even if you do not itemize your tax deductions2) it can lower your AGI, which may make you eligible to claim additional tax deductions or credits

-walkerRather than owning the properties in an LLC, borrow as an individual first to get the lower cost money and protect yourself with an umbrella liability policy. 

I could see this working if you tried it this way:-buy a very distressed property that somehow still qualifies as "livable"-perform a live-in-flip style operation, minus the flip at the end-do a cash out refi based on the higher value after renovationYou'll have to make sure your cost of renovations are much lower than the equity built.

That's strictly a cashflow mentality since he seldom assumed appreciation.Colorado is experiencing major appreciation, so you could lower your payback standards since your profits would come from appreciation.Finishing the basement: Assuming $15,000 to get an extra $250/month, that's a payback of 60 months or 5 years.

I ran into this problem once where the contract is $50K below appraisal, and they'll only consider the contract value.The way it turned out, I got a lot less from the bank than expected, but in the long run, it did me some good as my cash flow was better because of the lower mortgage.

Everyone says they want lower prices and will just wait but its never that easy. 

If you are not looking for low down payments, the benefits to house hacking are still lower down (20% for owner occupants to avoid PMI vs 25% required by many lenders).