The HML wants to be sure the borrower has the ability to complete the deal at break even, at least.

(Just my opinion)TIP: One of the greatest advantages of making frineds with other SDI owners is your ability to loan to each other form your IRA's as you are not disqualified parties.

You can't just hand out a check and go file a lien.If you fund this, pay the tax lien off from loan proceeds, don't give it to him.I also suggest you fully amortize the loan and qualify him based on his ability to pay, have the attorney do that.The borrower can pay all loan costs, points may not be allowed, ask the attorney, including attorney fees and filing costs. :)

A lot of people choose to set up the LLC when they buy the first property so they initial expense is not incurred before you actually own investment RE.Having it before does give you the ability/advantage of developing credit lines.

This is a pet peeve of mine, especially when it's a GC trying to convince me that he has "low overhead" to save me money. 9 times out of 10, the reason the guy isn't driving a $40k truck or doesn't have an office is simply because he can't afford it, and usually they can't afford it because they aren't really adept at running their business, which makes me suspect of their ability to run my job.

(I had one county send me a bill for the whole lot and made me collect from all 30 owners (that was not fun) but very soon we will be going through LLC's for this to then again "play it safe".

Often banks will request an operating income statement and rental survey be completed within the appraisal assignment, so they are concerned about the property's ability to churn rental dollars.

I am a newbie investor looking to invest in high cash flow multi families in Philadelphia in the hopes of also getting price appreciation and the ability to add value somehow.

I suggest not doing a Sub-To for a rental property, unless you have the money and/or borrowing ability to payoff an existing mortgage. 

I particularly like rental property performance analysis, ability to see each tenant's lease terms, payment history, security deposits, etc., and especially the integration with TurboTax, maximizing rental-related deductions.