But having that initial plan- hell, even a scribbled outline on a napkin; will give you something to pivot from when the market throws a curveball.

Put together a spreadsheet and compare the performance of the subject property if you keep renting it as is for the next 10 or 20 years versus if you rehab and refinance.

If you feel ambitious, you could try a BRRR strategy adding additional equity to the subject home and then taking equity out of it to pay off either the HELOC or if you decided to the refinance the primary residence. 

If there are any modifications to their current contract, ensure that the lease renewal is shared with them in advance, clearly outlining any potential changes.

So much propaganda they only list peer-reviewed medical journals outlining the data and conclusions http://www.dogsbite.org/dog-bite-statistics-biblio...it's not a conspiracy that most insurance companies either do not allow those breeds on properties they insure or the exclude damage done by those "vicious breeds" it's an actual, real and present danger and very applicable to the aspiring and actual professional property manager/investor.

Personally, I'm incredibly ignorant on the subject compared to others, but find it fascinating.

If I switch from blinds to rods, would I a) provide receipts for the rods and deduct in full - receipt furnished to tenant,  2) deduct cost of blinds as priced today but receipt would be for curtain rods, 3) deduct cost of blinds as outlined in the lease but provide receipt for curtain rods (explanation and receipt furnished) 4)  be forced to replace using the same blinds that were installed when tenant arrived n order to deduct. 

I may explain that while I’d like to buy/finance/invest in his property, I need to earn a certain return on my invested capital for the given amount of risk, and if not able to earn the return on the subject deal than I will on the next deal.  

The bill currently says any home that's not a primary residence that's rented for 90 nights or more is subject to commercial property taxation.

 I'm not opposed to subject to, but my fear is whoever I am taking over the existing mortgage from will not continue making the payments.You make the payments.