Ideally a HELOC is used for less then a  year project where you can refi or sell to pay back the HELOC. 5 years is a long time, things can happen and if you reduce the cashflow on both properties you'll be increasing the risk and having thinner margins.

Thanks Brett, it is my understanding that by buying a property of equal or greater value it would allow for maximizing the tax deferral, which is ideal, but not a legal requirement? 

I am currently working to find ideal properties.

Around year 7 or 8, ideally year 10, re-assess your equity and maturation of those debt notes and re-adjust how you invest to suit your needs. 

Some carriers require limited water damage coverage depending on the age of the property and age of utilities.I would recommend at least 25% (ideally more) when possible and if you're limited to 10% you should make sure you cannot purchase another policy for a similar price.

Our biggest problem is getting her out so we can do a proper rehab 60 days of dead dime waiting for her to vacate is not Ideal obviously. 

I deal with wholesalers every week on my fundings  or should I say I see their fee's on the HUDS every week.. if I see one come in that is just way to high  like a 50k purchase and 50k assingment fee I wont fund it..

I'd like the building to be within 10 minutes walking distance from a Brown Line L stop, ideally in Lake View, North Center, or Ravenswood.

I understand that it is less than ideal, but it is reality. 

This property would be for my in-laws to purchase and move into, but I'd ideally dovetail any success into finding investment properties as well.So far, I've driven around the neighborhoods my in-laws would ideally purchase and jotted down the addresses of the homes that clearly need some TLC.