I wasn’t going to go into a drag out fight, but I did want to push back a bit though so he didn’t think I was just a pushover since he’s there for three years and has already been more of a pain than most of our other tenants.

We all have stories of working with buyers and having them disappear to offer on a FSBO we showed, or go to new construction and 'forget' they've been working with us. 

Many will say its a pain to deal with, but I had no problems when we did ours.

It was time consuming and painful (for the shy folk) but was the most enlightening and informative exercise.

I have no idea why this is such a pain to get rolling. 

My stock broker cautioned me against loaning on a rehab, saying that a major change in the ARV of the house could spell pain for me.

The court system is built around pain, not justice. 

If you have the money to purchase the 4 unit, I would recommend going that route for your first investment because if one tenant moves out you won't fell the "pain" as much as if a single tenant condo were to go vacant.It's a great idea to have an expert walk through the property with you on anytime of investment  but if you cannot get a contractor before you make the offer most likely you will still have some time during you feasibility period to get that done.

The rules don't take effect for 6 months, but the message is clear.Cities want their hotel tax revenue.Cities don't want those big bad real estate investors to make too much money.Cities don't want rental inventory disappearing from the market.Don't make a highly leveraged 25 year financial commitment on the assumption that current market conditions will remain the same.I stay away from things that the general public get into and it seems everyone wants to rent out an extra room or home.

Feel your pain.