Providing you take care of any outstanding maintenance needs while you are homesteading the property and properly screen your new/first tenants (aka: don't get too antsy to get tenants over getting the right tenants), it should be a relatively pain-free process. 

Is it really shady to then issue more stock in the form of option to employees at a lower price while everyone pretends you've reduced outstanding shares and no one complains because the price keeps going up?

My situation - I own my own home in NY free & clear with no outstanding debts.  

Basically, do you evaluate the rental income against (1) the value of the home when you purchased it, (2) the outstanding mortgage or (3) the current estimated value of the home?

But she is suggesting very low payments ($100/month max.) that will take about 4 years to repay assuming no skipping and she will follow through.First question, can I charge her interest on the outstanding balance and fee for late/delinquent payment?

I've heard repeatedly from these damn podcasts that there is no " get rich quick" to this except in very rare cases.

On November 2, we received 1 months rent (so I guess we put that towards Aug outstanding rent and technically he is now just 4 days late paying November 's rent and everything else has been paid) His lease states after the 5th of the month there will be a late fee and after 10 days he will receive a 3 day notice to pay rent.

I am telling you that if I lived in Illinois this is what I would do, consequences be damned.

In that case, your calculation would be (Outstanding Loan Amount * (Interest Rate / 12)) = Monthly Interest Payment.

Regarding taking a 401k loan: You would have to confirm that your 401k plan allows for a 401k participant loan (and that you have not had an outstanding loan in the last 12 months).If yes, you can borrow up to 50% of the balance not to exceed $50,000.The repayment terms are equal monthly/quarterly payments (as you prefer) of principal and interest (e.g. prime + 1%) spread over a 5 year term (or longer if you will use the loan to purchase your primary residence).