Looks like we are going in circles and soon turn this thread into fairly recent on the same topic"Use HELOC to paydown mortgage fast" - https://www.biggerpockets.com/forums/49/topics/329...I trust @Chris May calculation and quickly running my own numbers see the same results:1) No magical secret: as amortized mortgage payment has no front-loaded interest, majority of "magic" works just by making extra monthly payments whatever the source or procedure it is.2) Using HELOC as expense account to "time" income-expense cycle only brings marginal benefits when compared to increased risk, extra bookkeeping  and complexity.

Level 1: An LLC formed in the state of the property for each investment.Level 2A: An Ownership Wyoming LLC holding company for all the equity of the multiple LLCs at Level 1Level 2B: A Management entity to facilitate legal/tax/bookkeeping/day-to-day ops/etc. for each Level 1 entity (goal to leverage economies of scale against overhead cost of local third-party contractors, vendors, software subscriptions, etc.)Level 3: MyselfI feel with the layers described and proper legal & accounting I's dotted and T's crossed, there is a sufficiently thick corporate veil and there will be appropriate insurance for each entity to further protect from loss.

My mom was an book keeper for a PM. 

Things such as frequent drive-bys of your property, multiple calls to tenants about different issues, bookkeeping (there's a lot of bookkeeping), and so much more.

., complaints, bookkeeping, etc.  

Consider the cost of a manager to do this for your out-of-state friend, such as answering calls, bookkeeping, cleaning, emergencies, maintenance, etc., for all of those separate tenancies, when calculating the potential earnings.  

Then, although you're on call 24/7, most of your time is yours to manage the way you'd like to.Or a handyman/maintenance service you market to private landlords.This is probably beneath you, but resident managers who can handle maintenance, as well as manage tenants and handle bookkeeping are very rare and in demand.There are so many different types of properties who need them.

I guess I'm just wondering how people use Evernote here with property management/ investing.I'm trying to implement a new system for self-managing properties/ accounting/ book keeping

Quickbooks Online. .50 for ACH transactions, recurring templates, etc. plus all of your bookkeeping.

It took months and help from a friend in the business to get the bookkeeping sorted out.