At this time in the economic cycle I'd start small.

Plus, the stock market crashed in 2008 too so it's not like your investment is safe there depending on the economic cycle.

Again, ALL CREDIT FOR THESE TIPS GOES TO J SCOTT. https://www.biggerpockets.com/blog/biggerpockets-podcast-311-rules-investing-real-estate-coming-economic-shift-jscott/Along with J, do you have any tips for RE investors in the current market?

@Bryan Champ You should definitely look at the economics including the supply and demand for affordable housing in the town.

Hi, I own 2 rental properties(1 is SFR and other is a duplex that we are house hacking and living in one side) and have a few questions as I try to get a financial system in place to implement as the business continues to grow:1) What is the best system to keep track of my finances and the health of my "business"? 

If you are ok with waiting until you are 59 1/2 years or older to have full access to the 401k contributions and gains (penalty free) than your path might look different than someone who wants to have a monthly passive cashflow that meets or exceeds their monthly expenses by age 40.Trying to amass a large nest egg in financial products such as a 401k, IRA, etc will require you to save & invest 50% of your income to gain 1 year of paid expenses in retirement, which assumes similar health status and lifestyle choices once you get there.If you are interested in economic independence earlier rather than later, invest only the 5% to get the full employer 401k match and then focus on positive cashflow investments to start replacing your active income (your job).

It states that the title was never in the previous owners name due to his failing health and he owed back taxes on it and that my friend was responsible for paying those taxes and transfering the title.

Although it’s difficult I don’t let myself get sucked into the personal affairs of feuding tenants as I'm not their mental health counselor or divorce mediator, I’m just there to run a business.  

The housing market is currently very healthy and we have no reason to expect a housing crash even in the presence of an economic recession, so for those reasons I believe it is a great time to buy.

@Ethan Smith unless this is large multifamilyYou’ll probably find 24 hour surveillance isn’t economical