A 1,000 sq ft cabin when you have 300k into the lot just won't cut it. 

Microsoft Excel, and most budget or free online bookkeeping isn't going to cut it in this situation.For the rental properties you own directly, I often tell clients and prospects that a P&L in Microsoft Excel is just fine and a balance sheet is not necessary for tax purposes. 

Many borrowers think they can “cut out” the middleman (mortgage or loan broker), save some upfront “points” and fees, and go direct to a lender.  

Many companies will be lazy/cut costs after they have a large enough customer base.Currently Dataskip.io is the best. 

A huge number of properties we have looked at would have issues on this front.It can lead to an opportunity to improve the value of a property if you can buy it with an illegal area, get that area legalised and then sell on with a higher value that the bank would lend against, but it's not clear cut and it seems though that there are almost two levels of 'legalisation' - we were able to register all of the annex on the plans and could fully incorporate a portion of it but there is another portion that is too close to the back boundary wall that should only be used for things like storage and not ever for habitation. 2) During the purchase process be careful, amongst other issues with this property we had the situation where the seller's lawyer was not actually a lawyer (having been struck off).

Further, I had negotiated 12 months interest reserve; they cut that to 3 months.  

Should I just hire a tree service to clear a path and cut the dead tree?

I am not sure if it was just my market or more on their end but at the end it was a pretty big loss for us, so we cut it. 

Are most of those gurus just selling courses/cutting a fee on top of an agent?

If you thinking there is some "giant" "fat" to cut out of Real Estate transactions I'm sorry it just is not true.