If something urgent does arise, it helps to have a local STR manager that can handle it for you rather than larger national companies like Vacasa and Evolve - that tend to be notoriously bad at handling issues for owners.

I have spoken with Quicken developers @ Intuit and they know about couple issues we found, but it is not on their top of the list. 

Sometimes they have none, but usually they don't like to go below 6 months due to how loans are bought and sold on the secondary market with traditional lendersFor Cash-outs, due to risk and appraisal issues, they don't like to go below 1 year seasoning period.

What have been your biggest obstacles or issues that youve had getting started or with your current business?

If it is large or there is a shed then it is less of an issue but people often use the garage for storage as well

Needing money is ALWAYS an issue for us as investors. 

One of the main reasons that jobs end up having issues is because no one told that Contractor about _______ and it gets missed in the original bid.

Gordon,You need to find out if there are any Environmental issues (either actual or potential). 

I don't have any mentors to guide me, so even gaining that would be a huge step towards me becoming successful.Potential investors, those who's been through these issues, please advise me on what I can do to just start my property investing journey!!

It's on a block lot, no foundation issues were identified.