That being said, do I need a booking system to keep my rental organized with bookings or do I just list it on a site like Airbnd or VRBO?

I want to understand a little more before asking the next question.So far my basics are:Crowdfunding has to be done through another organization, must be under $5 mil, has a limit of non accredited investors in a 12 month period and still requires filing with the SEC.506(b) can have up to 35 non accredited people - Great, I can't publicize to the general public, a few other rules should an accredited investor want in that I am still trying to hash out) and in general does not need to be registered with the SEC.506(c) must use accredited investors and that one item tells me to look no further into this one for now.I am still digging into Reg A but it looks promising as does the 506bThank you. 

How large or small of an organization do you want to build?

Your suggestions could work, but what jumped to mind for me is that there are a lot of organizations that could partner with you for boots on the ground knowledge.But the answer really depends on what you feel your unique ability is.

Like I said finishing the basement would allow you to charge more for the additional space too, and you will need to furnish the units if you go the STR/mid term rental models.Since you're in college you should definitely network with other students at organizations for business students, entrepreneurs, etc.

Organize your current finances.

It's designed to be a win-win...the service member gets the opportunity to build their skills & resume for their transition to the civilian sector, and the company gets a 6-month 'working interview' with a potential employee who brings valuable work ethic and leadership to the table.There are quite a few real estate companies that are already vetted SkillBridge partners...if you were able to do an internship with one of those companies it would provide you some valuable experience and training, while still having the 'safety net' of being on active duty until your date of separation.The site with some additional info about the SkillBridge program and the list of approved companies is at:  DOD SkillBridge - Authorized SkillBridge Organizations (osd.mil) 

If it's a larger organization, feel free to inquire about their staff qualifications.2.

But, depending on the property you’re buying, you may not need to review every single one of these (this is where a real estate agent or broker can be helpful as well):Population and job growthHousehold median income trendsAccess to public transportation and amenitiesNeighborhood and school rankingsUnemployment rateCrime rateBusiness openings and closingsNew development activity that could help or harm your intended investmentProperty value trendsFair market rent trendsPercentage of renter-occupied householdsMarket vacancy trendsGross rent collectedMaintenance and repair expensesUtility expensesProperty management, leasing, and advertising feesInsurance expense including past insurance claims, need for flood insurance, and the cost of homeowners and landlord insuranceProperty taxes and potential increase due to change in ownershipProof that any sales tax collected on rent has been remitted and is up to datePhysical property inspections including structural and mechanical, wood-destroying organisms, radon, and lead-based paintTitle commitment on the property and legal descriptionMost recent ALTA (American Land Title Association) surveyZoning or use certificate for property in rural or unincorporated areasNew survey, septic report, and well water report for rural propertiesPhase I environmental report for property near industrial areasHOA covenants, conditions, and restrictionsHOA financial reports including P&L and balance sheetReview of seller financial statements including a copy of the seller’s tax return to verify income and expenses are true as reported to the IRS going back two or three yearsReview of tenant file including the lease terms and conditions, deposit amount, tenant application, and background and credit checksCopies of existing service contracts such as landscaper or current property managerList of all outstanding invoice and proof of payment for all work recently doneLien search to verify there are no existing worker’s liensHistory of insurance claims on the property going back three yearsVerification that property appraisal is for at least the contract purchase price if not moreCompare your pre-offer pro forma analysis to the seller’s reports to make sure the deal still makes sense.Good Luck!

The LLC agreement is not the same as the articles of organization for a corporation.