The fact that you state something cant be done shows your lack of effort to spend your customers wisely!   

I think it's more about adhering to contract law and being careful to not violate agency laws.

Perhaps you're simply lacking information that can be gained by doing some projects with others, doing what you wish to do.

The Assessments levied by the Association shall be used exclusively for payment of Common Expenses including, without limitation (i) the upkeep, maintenance and improvement of the Common Areas and other maintenance obligations set forth in Sections 10.1 and 10.3 below; (ii) maintenance, repair, replacement, and operation of rights-of-way and easements within or immediately adjacent to the Project (e.g. landscaping and sidewalks within the right-of-way of adjoining streets) to the extent that such actions are required by government entities or deemed appropriate by the Board, (iii) promoting the recreation, health, safety and welfare of the Owners and other lawful occupants of Lots within the Property, (iv) payment of property taxes for the Common Area; (v) insurance premiums; (vi) legal and accounting fees; (vii) management fees; (viii) charges for utilities and other services provided to the Common Area by the Association, if any, and for all utility charges paid or incurred by the City and reimbursed by the Association for street lights in the Common Area; (ix) costs to maintain the entrance features, including any electricity, landscaping and irrigation expenses associated therewith; (x) the performance and exercise by the Association of its rights, duties and obligations under the Project Documents, and (xi) maintaining any Stormwater Control Facilities located on portions of Common Areas to the standard required by the governmental entity or agency having jurisdiction over such areas.

If you have certain skill set but lack the other, are you confident enough in yourself in terms of motivation, learning capability to learn the new skills you need to become successful in the field you want to be? 

Too few details to answer (Of course this varies county by county, all questions could be answered by reading the (zoning)/building code and/or clarified with a visit to the county planning office).but some clarifications because: lots of things are "tiny homes" but what you describe small houses "on permanent foundations" needs to be clarified , tiny homes could be:-stick built, see below. check your county code/planning dept-stick built cabins/recreational, a specific zoning and potential occupancy/etc restrictions but worth looking into where the zoning allows for it -hud manufactured homes (smaller singlewide perhaps 400sq ft 600sq ft minimum)-non-hud park models (on axles), ansi standards- other "RV's" built on a chassis:  organizations, state agencies, etc - will certify factory built (or sometimes inspected professional built) tiny homes on chassis - to whatever standards ansi, riva, dot/ l&i?

There are great agencies out there that let you keep 100% commission and you may have a nominal monthly fee based on your commission.

The biggest hurdles, obstacles, and challenges in life that limit your belief and mental structure in no particular order:1)Thinking where you start is where you finish.2)People resting or stopping in the middle, not at the end. 3)Prioritizing instant gratification rather than delayed gratification4)The controversial mark twain  quote or not quote--It ain't what you don't know that gets you in trouble, it's what you know that ain't so.5) The lack of an ability to move on.6) Not appreciating the power of delegation.There's probably 2-3 others I am missing, but over time these have rang so true in any instance I have faced in life.

I am an owner/operating partner of a local title company (Legacy Title Agency) and we have come across quite a few fraudulent and suspect deeds in the city of Detroit. 

Hope you weren't planning on a lot of short term rentals. lack of wifi access would be a bummer.