Which is why I pay more, for less cash flow in highly desirable areas.In high income areas, rent is a lower proportion of income so therefore your tenants have a higher capacity for paying higher rent because rent is less than 20% or even 10% of their income.

Choose the Right Property:When choosing a house to flip, search for properties in desirable neighborhoods that need structural or cosmetic improvements.

There are other ways to legally raise capital, however, they have some inherent disadvantages making them considerably less desirable for what you’re trying to do.   

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

We were especially thrilled to start our investing journey with a duplex, and it was even better that the tenants desired to stay and had been consistent with rent for many many years.

If it's a deal that is in a very very desirable location and has tons of built in equity and appreciation, I would be totally good with negative cash flow for Y1 and Y2.

So I get your hesitation to be too demanding and your desire for the problems to go away as fast as they can, however since you have NO property manager ( I don't use one either), it is incumbent that you take a more ACTIVE approach with management of your property.Let's review your situation.  1st time leak occurred, you sent a plumber over to find the problem.  

Owner occ developments there is no value associated to the income approach so these props generally speaking will appreciate a lot more as the neighborhoods are much more desirable. builders the last thing they want to do is sell to investors if they are creating owner occupied communities.. rentals degrade the neighborhood and they will be sabotaging their own values to allow a bunch of investors to buy and rent out in their communities.So when you buy new builds keep in mind if its a build to rent community they will NOT appreciate like owner occupied neighborhoods.. might be best to find something already 3 to 5 years old where the stigma of renters dies down.. that would be best to protect your investment.

Still has lots of belongings (including a boat) in a large shed on the property... could imply intention to move back, or a desire to not have to deal with it and possible interest in having help getting rid of all this stuff3.

Playing sports isn't forever and I know a 9-5 isn't for me, I am very much desiring to get ahead and learn how to build wealth from all those smarter than me!