Michael and Thomas mentioned some of the benefits/ drawbacks of inherited tenants/ some of  the things to be careful when in such a situation.One way to know what your property might rent out for is checking local rental listings on Craigslist, apartment.com and other such websites.Good luck and keep asking your questions on BP!

I don’t want to disrupt this exchange of money by being legalistic, I Just thought there is a way to transfer the property into a legal entity and start to take advantage of those tax benefits!

When you structure a contract that passes enough of the risks and benefits of ownership to the other party the IRS can deem that a sale happened even if there was not actual change of title. 

Will the capital improvement benefit the entire building as a whole? 

As much as the people in your list above are essential, what is more essential are individuals who are currently doing the type of investing you want to do.Putting these people on your team first as mentors will help you put your best foot forward when you pull the trigger on the first investment.These mentors can also give you advice on the best contractors to use, agents to use, and CPAs/Tax Advisors.

If you were to apply income based valuation on 1 to 4 unit properties, you would likely get the wild swing that you have observed.Second, the formula of "Net Return" as you defined it (i.e never seen it used before) is essentially Cap Rate * 5 (i.e. using your assumption of 20% down).

Essential I have 1 rental that brought in $8750But between all my expenses I am seeing a total loss of approx. $17,000 between flights, office supplies, ect. 

But, if you have a bad tenant, you can go through the 14 day notice, wait out the 3-4 weeks court day and the day before you go to court, they can deposit some cash in the account, then show up at the hearing and say they made a payment and you accepted so therefore the 14 day and court hearing is  essential void. 

Essentially, reviewing building plans with the guys at the planning counter.

I see you are from Illinois and here is a link to their state website explaining that the property tax exemption is only on the primary residence:https://www2.illinois.gov/veterans/benefits/pages/real-estate.aspxHere is a breakdown of these laws by state:https://www.hadit.com/disabled-veterans-property-tax-exemptions-state/Thank you sincerely for your service to our country!