But, I'm concerned about that much work, which means that much risk and money I need to find, may be being clouded by the idea of convenience.So, my question is: Does anyone here have benchmarks or flags when they say, "I'm to going to much on emotion and making to many trade offs."?

Or give a "workshop on real estate investing for medical professionals" at an industry trade show - try the smaller, local shows first to build up your reputation in the medical industry. 

My rents are lower, but, life can go on because I trade Futures for Daily income.

This is what can be done in Illinois: Answer the telephone, take messages, and forward calls to a licenseeSubmit listings and changes to an MLSFollow up on a transaction after a contract has been signedAssemble documents for a closingSecure public information documents from a courthouse, sewer district, water district, or other repository of public informationHave keys made for a company listingDraft advertising and promotional materials for approval by a licenseePlace advertisingRecord and deposit earnest money, security deposits, and rentsComplete contract forms with business and factual information at the direction of and with approval by a licenseeMonitor licenses and personnel filesCompute commission checks and perform bookkeeping activitiesPlace signs on propertyOrder items of routine repair as directed by a licenseePrepare and distribute flyers and promotional information under the direction of and with approval by a licenseeAct as a courier to deliver documents, pick up keys, etc.Place routine telephone calls on late rent paymentsSchedule appointments for the licensee (does not include making phone calls, telemarketing, or performing other activities to solicit business on behalf of the licensee)Respond to questions by quoting from published informationSit at a property for a broker tour that is not open to the publicGather feedback on showingsPerform maintenance, engineering, operations, or other building trades work and answer questions about such workProvide securityProvide concierge services and other similar amenities to existing tenantsManage or supervise maintenance, engineering, operations, building trades, and securityPerform other administrative, clerical, and personal activities for which a license is not requiredIn Illinois, an unlicensed assistant may NOT perform the following tasks:Host open houses, kiosks, home show booths, or fairsShow propertyInterpret information on listings, titles, financing contracts, closings, or other information related to a real estate transactionExplain or interpret a contract, listing, lease agreement, or other real estate document with anyone outside the employing licensee’s firmNegotiate or agree to any commission, commission split, management fee, or referral fee on behalf of a licenseePerform any other activity for which a real estate license is required

She claims that the mold made her sick but did not report it right away and made it difficult for the trades to fix the issue. 

I traded in some of my single family homes and duplexes in the rougher areas of my portfolio and acquired some larger assets in the suburbs)1,000+ units under management.

Virginia Manufactured and Modular Housing Association8413 Patterson AvenueHenrico, Virginia 23229The state trade association for sellers and community owners.

What should I say to not let her thinking this is a trade.

I'm buying in Atlanta now and may swing my way to Memphis next year.  

There is a trade off here...managing 4 properties is more work than managing 1.