However, in the very limited circumstances too complicated to go into here, the payroll aspect of the S corporation may allow a high income earner to pay himself enough to decrease his taxes via (1) payment into a retirement account and or (2) qualify for the 20% write-off for unincorporated businesses.  

You will want to start with a cover letter then attach to a business plan that goes over at least the following:Mission Statement - including executive summary and financial overview.Business description - name and location of business, principal owners, legal structure, status and type, definition of products/services, major strengths and challenges, strategic goals and objectives.Operation Plan - location, physical facility, labor, suppliers.Market Analysis - industry trends, description of total market, target market, analysis of competition, production/services differentiation.Sales Strategy - Pricing policy, distribution, promotional efforts.Management Profile - personal history of key participants, duties and responsibilities of key participants, compensation, available resources.Financial Analysis - sartup costs, source and use of funds, capital equipment list, income statement projection, monthly cash flow projections and assumptions, balance sheet projections, personal financial statements, personal income tax returns.It all a numbers game - make sure you present your number truthfully and make sure you educate yourself on every aspect of the business.

Achieving the extraordinary is not a linear process, the secret is to put in the time every single day on meaningful tasks and to work through the many frustrating aspects of the journey. 

I am trying to determine two things:  Which app is best for helping me manage the financial aspect of my RE Portfolio (I currently own 30 doors, mostly 2-4 unit multifamily).  

More is better, but go with whichever one you can make work.Nothing that requires too much rehab, because your budget will end up being way more than you expected, and you can do that on some future project.This will eliminate your living expenses because your tenants will be paying your mortgage, and it'll teach you how the real estate business works: finding and analyzing deals, screening and managing tenants, the business aspects of it like taxes and accounting, how to do small repairs, and lots of other stuff.The reasons you should move in (instead of having it as an investment property you don't live in) is because you can keep an eye on things, any problems that arise are not too far away, and especially: you can put a tiny down payment on the house if it's owner occupied.

In going up it was due to the roof line and there being an attic space.Adding a room on by going out needs to consider existing configuration and aspect to enhance flow and comfort of the layout.With a big lot then going out seems the most obvious solution but what are other homes like in the area?

Another aspect of the plan I didn’t add is just like someone using leverage would buy single family homes will they can buy a multi family.

The other aspect to consider is how long you have been friends.

If the Association is well run, major expenses are generously accrued for, and there are no onerous rental restrictions, I wouldn’t be concerned about that aspect.

Only you can really answer what aspects you prefer.