I'm assuming if I replace the roof it will be a more valuable property.

Hi,I was wondering if anyone has any experience with renting a more expensive home to executives or high net worth people?

Now I have an Escalade and want to have a more classy advertisement.

Maybe because I worked as a subcontractor and had GC's constantly trying to cut my throat, I take a more aggressive stance when someone tries to take my money, just because it's there in front of them.

Not everyone does good work and I don't want to risk having a more expensive fix later or more damage because of their shotty work.I always use property managers and I've found the best way to keep costs minimum is to have an awesome manager with killer connections for good work for low prices.

For larger projects, then a more formal Syndication / LLC is probably a better option.Good luck and congrats on your success!

But there's another way of looking at it:He can buy a cheap house right away and start getting rents, while a more expensive house might only be possible in 10-12 months.

Its a more analytical approach but it worked for me...

Real Estate is really my long term plan for retirement, preferably sooner than later :) I am most interested in buy and holds as I like the idea of a more “passive” source of income over the long term.

I ask because not knowing you, your personality and experience, it sounds like having a more "battle hardened" LL help you out might be beneficial.