I am wondering if it makes more sense to just deal with the large upfront cost to have the roof done fully or if repairing the damage will end up coming back to haunt me.It's a rather small house at just over 600sqft, for an addition is it really just a matter of getting estimates for the addition and comparing that to the additional rent I would get and seeing if it's worth it?

i am starting my real estate journey and I am interested in investing in real estate to create some passive income but more importantly to escape the 9-5 jobs and create generational wealth.

A few additional items to help you: 1) If you have a Roth IRA, a Roth IRA can't be rolled into the Solo 401(k), only pre-tax funds.

When a seller has a mortgage on the property you can't do a lease  option for more than 6 months but you can do a Wrap or Land Contract.

More interested in Tyler than the other two though 

I am in the Houston area and my primary goal is to become financially free and look to enjoy more quality time with my family as I do want to move away from the day to day desk job.

That helps.

I wanted to consolidate banking to a credit union as I am investing much more in real estate and SMBs.

I’ve made some valuable connections here and picked up a lot of helpful advice from the forums.I’m an investor and real estate agent in the Grandstrand area, so we might even have opportunities to help each other out in the future.

It's more to do with the timing.