Instead of putting a new 2 pitch roof on I decided to say screw it and let’s do a 6 pitch, which reduces snow load and makes for a better overall product. 

This is the only time I would advocate loading up on credit card debt if you are wise about it and either invest that money, or use the money to pay off other debt such as your car loan etc. 

Yes tenants can be a PIA at times, but if the communication is clear and expectations are front loaded, I think some of these heartaches can be avoided.

This is worth its weight in gold. 

Also, this is something that has been discussed at length on BP, use the search feature and look at old posts for loads of good advice.

Having a long term tenant who pays  is worth their weight in gold.  

@Dennis Abad-Jimenez, that's a loaded question. 

Don't load someone up, make them aware of what's coming up and negotiate in advance, but don't commit work to someone until they finish the project they are on.If you browse BP posts, note that most contractor problems with someone new is locked in with a single contractor on the entire scope of work for a project.

He is trying to decide between the following options:1 - Sell house in MA and use majority of proceeds to pay off high interest debt.2 - Rent out house in MA which would cash flow approximately $300 per month after mortgage is paid.The debt load is credit card debt and fairly significant.

* Greed - The housing market is sky high - jump on your chance to cash in and load up your bank account...* Sloth - Weighted down with endless home projects?