She offered to pay a full rent's payment upfront, along with the deposit, to compensate for her current unemployment.Are there negatives or major red flags that are associated with this that I should consider as I evaluate her application?

@Adolphus Fletcher For multifamily investing, most real estate investors typically use an LLC for several reasons:Liability Protection: LLCs protect your personal assets from lawsuits or debts associated with the property.Pass-Through Taxation: Income and losses from an LLC pass through to your personal tax return, avoiding double taxation seen in C-Corps.Flexibility: LLCs allow for flexible management structures and are easier to maintain than corporations.Anonymity: In some states, LLCs can offer a degree of anonymity if you use a registered agent and form the LLC in a state that doesn’t require public disclosure of members, such as Delaware or Wyoming.S-Corps are should be avoided for real estate investing because of various reasons.

AND, for the items we did get at HD, I had a corporate account and weekly everything was ran through on purchases for my corporate pricing that in-store associates, even pro-desk, has no access to other than seeing what corporate sent them for my invoice. 

Real estate can be unpredictable, so having a diversified portfolio can provide more stability.Key Lesson #4: Understand the True Costs of Ownership Another critical lesson was understanding the true costs associated with real estate ownership.

The mold remediation companies I've contacted (Tallahassee, FL) have quoted me $700+ to survey the home and create a detailed report however I'm not sure the home cleaning services will actually remove the mold well enough to keep it from coming back.

A great way to start is by attending RE events and joining a local investors association.

Some people have other income sources such as Social Security, pensions, etc.

Paying off a property early will have an opportunity cost associated with it.

If you pay rent while in Aspen, that housing expense will be factored into your DTI ratio (e.g. total rent paid in 5 months divided by 12 months).You should be prepared for your loan file to go to an underwriting manager for second-level review on account of the occupancy risk associated with your primary home being located so far away from your work.

Just set up a nice place, air,vrbo and direct and the rest takes care of itself(considering you are investing in place where STR are allowed and have done associated diligence)