Largest non-profit trade association that advocates for landlords and property owners in MA.

I don't want to always trade my time for dollars as I currently must do in my profession.On a recent BP podcast, they talked about the triangle of success in real estate being Knowledge, Capital, and Hustle (hard work).

If it is too high to trade for a larger property go the other way for something lower than what you sold for even if you have to pay capital gain for the variance the capital gain tax is greatly reduced starting this year. 

“While we support new entrants to the sharing economy and the competition it brings, we must be aware and very cautious of the negative impacts and repercussions,” said David Drennon of the Phoenix-based Arizona Lodging & Tourism Association, which lobbies on behalf of trade groups including the Southern Arizona Lodging & Resort Association.Drennon said his organization has no quarrel with a homeowner who occasionally rents out a guest house or spare room for extra cash.

These types of properties typically only trade when the market is nearing the top, making it a challenge if forced to sell.

Something Like hey I want to do a 1031, I have some land, but I want to trade it for a house, I think I can do that but wanted to make sure.......... goes a lot further than a generic I don't want to pay taxes on my land when I sale it, how do I do that.

This section prescribes rules for tracing debt proceeds to specific expenditures.Treas Reg §1.163-8T(a)(4)Treatment of interest expense(i)General ruleExcept as otherwise provided in paragraph (m) of this section (relating to limitations on interest expense other than the passive loss and nonbusiness interest limitations), interest expense allocated under the rules of this section is treated in the following manner:(A) Interest expense allocated to a trade or business expenditure (as defined in paragraph (b)(7) of this section) is taken into account under section 163(h)(2)(A);(B) Interest expense allocated to a passive activity expenditure (as defined in paragraph (b)(4) of this section) or a former passive activity expenditure (as defined in paragraph (b)(2) of this section) is taken into account for purposes of section 469 in determining the income or loss from the activity to which such expenditure relates;(C) Interest expense allocated to an investment expenditure (as defined in paragraph (b)(3) of this section) is treated for purposes of section 163(d) as investment interest;(D) Interest expense allocated to a personal expenditure (as defined in paragraph (b)(5) of this section) is treated for purposes of section 163(h) as personal interest; and(E) Interest expense allocated to a portfolio expenditure (as defined in paragraph (b)(6) of this section) is treated for purposes of section 469(e)(2)(B)(ii) as interest expense described in section 469(e)(1)(A)(i)(III).Treas Reg §1.163-8T(c)(4)Allocation of debt; proceeds deposited in borrower's account(i)Treatment of depositFor purposes of this section, a deposit of debt proceeds in an account is treated as an investment expenditure, and amounts held in an account (whether or not interest bearing) are treated as property held for investment.

I agree with the comments above that most of the suggestions are basically you trading your hours for dollars. 

Or should I just try to find another jack of all trades maintenance person?

@Evan Coburn The only exception is if you recently graduated from a college/university/trade school (e.g.