@Katelin UhinckIf the commute is an issue you could buy a property that cashflows to go toward personal expenses and still have the long term benefits of having renters pay off the mortgage.

@Ashley DennisI think people should consider owning real estate personally (tax benefits) and inside of their retirement account. 

He's a driver so also stays in hotels often and isn't at home as much as other people.One benefit of me renting to him is that I was going to leave most of my stuff in the unit to rent furnished and will grab what I am ready to take slowly.

I think it's a solid strategy that offers ample benefits.

Late fee is considered reasonable if it is not more than 12% of the rent for the rental period under the lease for a dwelling located in a structure that contains not more than four dwelling units or 10% of the amount of rent for the rental period under the lease for a dwelling located in a structure that contains more than four dwelling units or the late fee is more than the applicable amount but not more than uncertain damages to the landlord related to the late payment of rent, including direct or indirect expenses, direct or indirect costs, or overhead associated with the collection of late payment.A late fee may include an initial fee and a daily fee for each day any portion of the tenant's rent continues to remain unpaid, and the combined fees are considered a single late fee.

This is going to be my first STR learning experience if I eventually decide to kick start this journey, instead of just doing the buy and hold LTR which has less tax benefits. 

Benefits for my sister:- She gets into home ownership without any cash up front because I paid all the money down.- She starts building equity on her unit rather than renting. 

We are interested in appreciation, short term/mid term rentals but also tax benefits that come with real estate. 

I've heard about LLCs for a little while(Wyoming being the most popular) and the tax and liability benefits that come with it.

Connecting with investor-friendly experts and potential business partners is a smart move, and the Northern Virginia real estate community is sure to benefit from your expertise.Best of luck investing!