Meaning both properties (Primary residence and investment) are investment vehicles to get you somewhere long term.  

i have started using an app called Everlance. i like it very much so far. it tracks mileage and expenses. it allows you to set up favorite locations and different vehicles. it has categories for personal, work, and medical. the expense tracker allows you take photos of the receipts so i don't have to have large stashes of paper for long periods of time. as for paying for things, i do have an llc and business checking/savings however there is very little money in there as we are just starting out. most of my expenses have been put on 2 personal credit cards or paid from my personal account. i knows it's a bad idea but currently have no other options.   

My list of requirements includes concealed parking that can fit 5 vehicles and no HOA - I think I'll also introduce myself to the neighbors to get a feel for the overall personality of the neighborhood before buying.  

Examples include office space, machinery and equipment, vehicles, computers and peripherals, and real estate.Besides renting the assets personally, you may use a multiple entity arrangement such as partnerships, S corporations or limited-liability-companies to rent the assets to a corporation.

Placing the ownership of a property in a limited liability vehicle is a good backup option to insurance.

Preferably they arrived in a clean, well-kept passenger car that is in a clean condition.Now who was driving the vehicle?

The only problem is vehicle expense I use to travel to and from the various houses for fix up and renovation.

Such as converting from a annual lease to a month to month, or to catch up with market rent rate for that neighborhood...but I wouldn't raise the rent because their chance of paying rent on time is now relatively lower than before the father lost their job.I would do whatever it is necessary to convey to them paying rent should be their #1 priority, before they pay for their leased vehicles, before they pay their cable TV bill, before going out to dinner...

@Danny Diaz In my experience, REITS have been an excellent investment vehicle, particularly in 2014 (took some time to speed up, corporate stocks did much better in 2012-13).

Some properties went from on revenue stream to 4 different ones...4- I use the business of REI and created an LLC to defer some of the profits through to family members to help pay for their college as they are "employees" of my REI business and I can deduct (pay for their college)  As i can use about 5k a year as education expenses. 5- Since my siblings are employees of my businesses and are in sales and marketing for the business they use a wrapped (lettered in advertisement) company vehicle going back and forth to school and other business related venues.