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All Forum Posts by: David Dachtera

David Dachtera has started 94 posts and replied 4493 times.

Post: Milwaukee Landlord Bootcamp - full day of legal training

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Marcus Auerbach:

The venue address might not be accurate.

Post: What is the cheapest STR or LTR I can buy that will give me positive cash flow?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Lenny Reinstein:

Even though I am almost 50 and work in finance in NY, I have zero practical experience with the real estate investment. Dreamed about real estate investing fore years... 

I would like to buy my 1st property and try it out. I cannot be in FL to manage, so will need to hire a management company.

And don't want to start with a large loan. Want to start small. Where could I buy a studio or 1br that is a ready to rent condition that would make sense with the current interest rates and market situation,  and what would be the price range? Would love your advise. 


As I'm sure you can imagine, the purchase price is not what determines the cash flow, though it does play a part.

You'll need to study up on analyzing properties so you can answer your own question.

Also, real estate investing is one thing. STR is the Hospitality Industry has has considerations of its own.

Lots of reading and studying to do ... :-) 

Post: $4,300 water bill... Any help would be appreicated

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Sean O'Brien:

Hey everyone, 

I've had properties for about 5 years now and have never had this happen to me before. We were charged $4,300 for ONE MONTH of water bills when historically the bill was about $100. There were no leaks, no damage or anything but the city changed the meter. 

Is there any way to fight this? Any advice would be greatly appreciated.  


Since the city changed the meter, it's most likely a misread. Contact the city and discuss with them. 

Post: First STR with $100k or less?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Jayme B.:

I feel like having another mortgage is a huge risk for us. I know how it goes - no risk, no reward. Thinking about covering the mortgage, cleaning fees etc and worry about the occupancy rates otherwise you come out of pocket for it gets me worried. I know you have to calculate conservatively as much as possible, but it would be nice to pick someone's brain that has done this before and knows a good deal when they see it. I don't have enough savings to practice haha.

I know my wife loves Orlando, but it seems that market is so dang saturated. We spend a lot of time there, so thoughts are that it would be beneficial.

What's a solid expectation for return on 80-100k investment per month doing STR?

Thanks for all the feedback.


Read up on "rent arbitrage". That is, rent the unit (SFR) with the understanding that you will be doing a hospitality business out of it, and charge enough per night to cover your costs and make some profit.

Yes - STR is NOT real estate investing! It's the Hospitality Industry.

My $0.02 ...

Post: Rookie Investor - STR looks appealing

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993

It's important to remember that real estate is only part of the STR business. You're actually getting into the hospitality business, not real estate investing.

What makes me say that? Ever heard of "arbitrage"? Some folks make a deal with a landlord - who may or may not be the owner - to rent their property with the understanding that it will be used for STR or MTR (LTR would be a conventional sublease). They pay rent of $X and rent it out for $X + $Y. My upstairs neighbor does exactly that. By the way - this is week #3 with no guest upstairs.

You'll need experience operating a hospitality establishment - motel, hotel, B&B, etc. - to fully understand that side of the business. You'll learn about the platforms - AirBnB, VRBO, etc. - as you go along.

My "expert" on the subject is Jermaine Massey.

Post: What is fair in this business?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Henry T.:
Quote from @David Dachtera:
Quote from @Henry T.:
Quote from @David Dachtera:

If you have good tenants / customers, the easiest and fastest way to lose them is to screw them over.

My $0.02 ...


If THE OWNER is not making the rent he determines is necessary, then who is screwing who? just curious.

Who made the new determination? The tenant? The owner? 


The landlord, he da boss.
While we're at it, I support 4 year term limits for tenants.

So, you like vacancies / turnover? Most of the LLs I know personally would rather avoid the expenses associated with turnover. 

Post: What is fair in this business?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Bruce Woodruff:
Quote from @David Dachtera:
Quote from @Bruce Woodruff:
Quote from @David Dachtera:

If you have good tenants / customers, the easiest and fastest way to lose them is to screw them over.

My $0.02 ...


How is raising rates to market and taking this chance to get your CapEx funded screwing over the tenants?


Have they been long term tenants who pay on-time and care for the property well?

Drive them away if you feel that will serve your needs. Make sure you "take your blinders off" first. 

That's not the point. You said we landlords were 'screwing them over' by increasing rent. If rents are at or near market and your CapEx fund is at it's proper level, then how is that 'screwing them over'...?

Well, again, it is in your best interest to keep good tenants versus replacing them because they left after a rent increase. 

You may feel that "market rent" or more is your due. So, it's a tough distinction: keep rents where they are or risk having a (hopefully brief) vacancy? Either way, you may actually be screwing yourself over.

Post: What is fair in this business?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Bruce Woodruff:
Quote from @David Dachtera:

If you have good tenants / customers, the easiest and fastest way to lose them is to screw them over.

My $0.02 ...


How is raising rates to market and taking this chance to get your CapEx funded screwing over the tenants?


Have they been long term tenants who pay on-time and care for the property well?

Drive them away if you feel that will serve your needs. Make sure you "take your blinders off" first. 

Post: What is fair in this business?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993
Quote from @Henry T.:
Quote from @David Dachtera:

If you have good tenants / customers, the easiest and fastest way to lose them is to screw them over.

My $0.02 ...


If THE OWNER is not making the rent he determines is necessary, then who is screwing who? just curious.

Who made the new determination? The tenant? The owner? 

Post: What is fair in this business?

David DachteraPosted
  • Rental Property Investor
  • Rockford, IL
  • Posts 4,612
  • Votes 2,993

If you have good tenants / customers, the easiest and fastest way to lose them is to screw them over.

My $0.02 ...