Excel sheets can become a big pain IMO.

*Tenant may request hard copies of Water usage records in writing at any time, please allow office several business days to fulfill this request.So far, we have not had any question about the determination of the bill and we do it manually, which is kind of a pain, but better than paying for their water out of my pocket!

There is also a tenant who has been there for 10 years who is a very big pain to the town, he and the owner say he is leaving due to the sale of the house but I know if he decides to stay, he has to go and in Massachusetts that isnt very easy.My situation is I have very good credit (760) but am self employed so conventional financing is tough.

Can you tell me about your day-to-day? and what you do.What is the most time consuming task for you? and did you overcome the obstacles? Let's share best practices! 

I share your pain regarding the cost of contractors.  

It may be a painful process but it`s worth it.  

But since that's limited to $100k, wondering if it's preferable (or possible) to count all that additional debt as acquisition debt for tax purposes.I figured HELOC was easier, less expensive, and less painful than doing a huge jumbo loan cash out refi, so figured I'd just do that to get in the game and learn my way around, and then could just do a cash out refi later on to both pay down the HELOC and make other new acquisitions.

Win, win, win.If all of your stock is currently showing gains, then selling it and taking the tax hit is way too painful in my opinion. 

@Stephanie Cabral,I 100% feel your pain, it's a really hard emotional situation.  

Happens to be my own office (commercial condo in a Medical building), so I've got a pain in the *** tenant :)Anyway, I created an LLC to pay rent to myself with and want to start off on the right foot with my record keeping.